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Clemens was inducted into the Boston Red Sox Hall of Fame in 2014, and was inducted into the Pawtucket Red Sox Hall of Fame on June 21, 2019.

Roger Clemens joined the Kansas Stars, a group of 24 retired major leaguers and his son Koby, to compete in the 2016 National Baseball Congress World Series. The team was put together by Kansas natives Adam LaRoche and Nate Robertson, and featured eleven former All-Stars, including Tim Hudson, Roy Oswalt, and J. D. Drew as well as Clemens. Pitching just six days after his 54th birthday, Clemens started for the Kansas Stars in a game against the NJCAA National Team on August 10, 2016. He pitched 2​⁄3 innings, allowing 3 runs with one strikeout in an 11–10 loss. On August 22, 2019, Clemens wore his Red Sox uniform and pitched in the Abbot Financial Management Oldtime Baseball Game, an annual charity event held at St. Peter’s Field in Cambridge, Massachusetts. The 2019 game benefitted Compassionate Care ALS, in memory of longtime Fenway Park supervisor John Welch, who died from Lou Gehrig's Disease in December 2018. Facing mostly young college players, Clemens pitched two shutout innings in the game, then moved to first base.

In January 2016, after Clemens once again fell short of the votes required for election into the Hall of Fame, former major-league star Roy Halladay tweeted "No Clemens no Bonds" as part of a message indicating no performance-enhancing substance users should be voted into the Hall. Clemens countered by accusing Halladay of using amphetamines during his playing career.

Boston came back from a 3–1 deficit in the American League Championship Series to the California Angels to advance to the 1986 World Series. After a victory in game five, Boston led 3 games to 2 over the New York Mets with Clemens set to start game six at Shea Stadium. Clemens who was pitching on five days rest started strong by striking out eight while throwing a no-hitter through four innings. In the top of eighth and with Boston ahead 3–2, manager John McNamara sent rookie Mike Greenwell to pinch hit for Roger Clemens. It was initially said that Clemens was removed from the game due to a blister forming on one of his fingers, but both he and McNamara dispute this. Clemens said to Bob Costas on an MLB Network program concerning the 1986 postseason that McNamara decided to pull him despite Clemens wanting to pitch. McNamara said to Costas that Clemens "begged out" of the game. The Mets rallied and took both game six and seven to win the World Series.

In 2013 Baseball Hall of Fame balloting, his first year of eligibility, Clemens received 37.6% of the votes cast, falling well short of the 75% required for induction into the Hall of Fame. He has garnered more votes in subsequent elections without reaching the 75% threshold; he received 59.5% in the 2019 balloting. With the inductions of Greg Maddux and Tom Glavine in 2014 and Randy Johnson in 2015, Clemens is currently the only eligible member of the 300 win club not to be inducted into the Hall.

On August 20, 2012, Clemens signed with the Sugar Land Skeeters of the Atlantic League of Professional Baseball. He made his debut for the Skeeters against the Bridgeport Bluefish on August 25, 2012, in front of a crowd of 7,724. It was the first time the 50-year-old had taken the mound in almost five years. Clemens pitched 3​⁄3 scoreless innings and struck out two: former major leaguers Joey Gathright and Prentice Redman. He also retired Luis Figueroa, who played briefly with the Pirates, Blue Jays and the Giants. Clemens allowed only one hit and no walks on 37 pitches in the Skeeters' 1–0 victory. Clemens made his second start for the Skeeters on September 7 against the Long Island Ducks. He pitched 4​⁄3 scoreless innings, with his son, Koby, as his catcher. He retired former New York Met outfielder Timo Perez for the final out in the fourth inning, and was named the winning pitcher by the official scorer. Clemens' fastball was clocked as high as 88 mph, and the Astros sent scouts to both of his outings with the Skeeters in consideration of a possible return to the team that season.

His first trial began on July 13, 2011 but on the second day of testimony the judge in the case declared a mistrial over prosecutorial misconduct after prosecutors showed the jury prejudicial evidence they were not allowed to. Clemens was subsequently retried. The verdict from his second trial came in on June 18, 2012. Clemens was found not guilty on all six counts of lying to Congress in 2008, when he testified that he never took performance-enhancing drugs.

Clemens was alleged by the Mitchell Report to have used anabolic steroids during his late career, mainly based on testimony given by his former trainer, Brian McNamee. Clemens firmly denied these allegations under oath before the United States Congress, leading congressional leaders to refer his case to the Justice Department on suspicions of perjury. On August 19, 2010, a federal grand jury at the U.S. District Court in Washington, D.C., indicted Clemens on six felony counts involving perjury, false statements and Contempt of Congress. Clemens pleaded not guilty, but proceedings were complicated by prosecutorial misconduct, leading to a mistrial. The verdict from his second trial came in June 2012, when Clemens was found not guilty on all six counts of lying to Congress.

After Washington prosecutors showed "a renewed interest in the case in the final months of 2008", a federal grand jury was convened in January 2009 to hear evidence of Clemens' possible perjury before Congress. The grand jury indicted Clemens on August 19, 2010, on charges of making false statements to Congress about his use of performance-enhancing drugs. The indictment charges Clemens with one count of obstruction of Congress, three counts of making false statements and two counts of perjury in connection with his February 2008 testimony.

On January 6, 2008, Clemens appeared on 60 Minutes to address the allegations. He told Mike Wallace that his longevity in baseball was due to "hard work" rather than illegal substances and denied all of McNamee's assertions that he injected Clemens with steroids, saying it "never happened". On January 7, Clemens filed a defamation lawsuit against McNamee, claiming that the former trainer lied after being threatened with prosecution. McNamee's attorneys argued that he was compelled to cooperate by federal officials and so his statements were protected. A federal judge agreed, throwing out all claims related to McNamee's statements to investigators on February 13, 2009 but allowing the case to proceed on statements McNamee made about Clemens to Pettitte.

On February 13, 2008, Clemens appeared before a Congressional committee, along with Brian McNamee and swore under oath that he did not take steroids, that he did not discuss HGH with McNamee, that he did not attend a party at José Canseco's where steroids were the topic of conversation, that he was only injected with B-12 and lidocaine and that he never told Pettitte he had taken HGH. This last point was in contradiction to testimony Pettitte had given under oath on February 4, 2008, wherein Pettitte said he repeated to McNamee a conversation Pettitte had with Clemens. During this conversation, Pettitte said Clemens had told him that McNamee had injected Clemens with human growth hormone. Pettitte said McNamee reacted angrily, saying that Clemens "shouldn't have done that."

In April 2008, the New York Daily News reported on a possible long-term relationship between Clemens and country music singer Mindy McCready that began when she was 15-years-old. Clemens' attorney Rusty Hardin denied the affair and also stated that Clemens would be bringing a defamation suit regarding this allegation. Clemens' attorney admitted that a relationship existed but described McCready as a "close family friend". He also stated that McCready had traveled on Clemens' personal jet and that Clemens' wife was aware of the relationship. However, when contacted by the Daily News, McCready said, "I cannot refute anything in the story."

On November 17, 2008, McCready spoke in more detail to Inside Edition about her affair with Clemens, saying their relationship lasted for more than a decade and that it ended when Clemens refused to leave his wife to marry her. However, she denied that she was 15-years-old when it began, saying that they met when she was 16 and the affair only became sexual "several years later". In another soon-to-be-released sex tape by Vivid Entertainment she claimed that the first time she had sex with him was when she was 21. She also said that he often had erectile dysfunction. A few days after the Daily News broke the story about the McCready relationship, they reported on another Clemens extramarital relationship, this time with Paulette Dean Daly, the now ex-wife of pro golfer John Daly. Daly declined to elaborate on the nature of her relationship with the pitcher but did not deny that it was romantic and included financial support.

There have been reports of at least three other affairs Clemens had with women. On April 29, 2008, the New York Post reported that Clemens had relationships with at least two other women. One, a former bartender in Manhattan, refused comment on the story while the other, a woman from Tampa, could not be found. On May 2 of the same year, the Daily News reported a stripper in Detroit called a local radio station to say she had an affair with Clemens. He also gave tickets to baseball games, jewelry, and trips, to women he was wooing.

Clemens unexpectedly appeared in the owner's box at Yankee Stadium on May 6, 2007, during the seventh-inning stretch of a game against the Seattle Mariners, and made a brief statement: "Thank y'all. Well they came and got me out of Texas, and uhh, I can tell you it's a privilege to be back. I'll be talkin' to y'all soon." It was simultaneously announced that Clemens had rejoined the Yankees roster, agreeing to a pro-rated one-year deal worth $28,000,022, or about $4.7 million per month. Over the contract life, he would make $18.7 million. This equated to just over $1 million per start that season.

Clemens made his 2007 return on June 9, defeating the Pittsburgh Pirates by pitching six innings with seven strikeouts and 3 runs allowed. On June 21, with a single in the 5th inning against the Colorado Rockies, Clemens became the oldest New York Yankee to record a hit (44 years, 321 days). On June 24, Clemens pitched an inning in relief against the San Francisco Giants. It had been 22 years and 341 days since his previous regular-season relief appearance, the longest such gap in major league history. On July 2, Clemens collected his 350th win against the Minnesota Twins at Yankee Stadium, giving up just two hits and one run over eight innings. Clemens is one of only three pitchers to pitch his entire career in the live-ball era and reach 350 wins. The other two are Warren Spahn (whose catcher for his 350th win was Joe Torre, Clemens's manager for his 350th), and Greg Maddux, who earned his 350th win in 2008. His final regular season appearance was a start against the Red Sox at Fenway Park, in which he allowed 2 hits and 1 unearned run in 6 innings, and received a no-decision. Clemens finished the 2007 regular season with a record of 6–6 and a 4.18 ERA.

Clemens was forced to leave Game 3 of the 2007 ALDS in the third inning after aggravating a hamstring injury. He struck out Victor Martinez of the Cleveland Indians with his final pitch, and was replaced by right-hander Phil Hughes. Yankees manager Joe Torre removed Clemens from the roster due to his injury, and replaced him with left-hander Ron Villone.

By the time Clemens retired from Major League Baseball in 2007, his four-seam fastball had settled in the 91–94 mph range. He also threw a two-seam fastball, a slider in the mid 80s, his hard splitter, and an occasional curveball. Clemens was a highly durable pitcher, leading the American League in complete games three times and innings pitched twice. His 18 complete games in 1987 is more than any pitcher has thrown since. Clemens was also known as a strikeout pitcher, leading the AL in K's five times and strikeouts per nine innings three times.

Clemens has received criticism for getting special treatment from the teams that sign him. While playing for Houston, Clemens was not obliged to travel with the team on road trips if he was not pitching. His 2007 contract with the New York Yankees had a "family plan" clause that stipulated that he not be required to go on road trips in which he was not scheduled to pitch and allowed him to leave the team between starts to be with his family. These perks were publicly criticized by Yankee reliever Kyle Farnsworth. Most of Clemens' teammates, however, did not complain of such perks because of Clemens' success on the mound and valuable presence in the clubhouse. Yankee teammate Jason Giambi spoke for such players when he said, "I'd carry his bags for him, just as long as he is on the mound."

On August 18, 2007, Clemens got his 1,000th strikeout as a Yankee. He is only the ninth player in major league history to record 1,000 or more strikeouts with two different teams. Clemens has recorded a total of 2,590 strikeouts as a member of the Red Sox and 1,014 strikeouts as a Yankee. He also had 563 strikeouts for Toronto, and 505 strikeouts for Houston.

Clemens said that he would retire again after the World Series but he wanted to represent the United States in the inaugural World Baseball Classic, which would be played in March 2006. He went 1–1 in the tournament, with a 2.08 ERA, striking out 10 batters in 8​⁄3 innings. After pitching in a second round loss to Mexico that eliminated the United States, Clemens began considering a return to the major leagues. On May 31, 2006, following another extended period of speculation, it was announced that Clemens was coming out of retirement for the third time to pitch for the Astros for the remainder of the 2006 season. Clemens signed a contract worth $22,000,022 (his uniform number is #22). Since Clemens did not play a full season, he received a prorated percentage of that: approximately $12.25 million. Clemens made his return on June 22, 2006, against the Minnesota Twins, losing to their rookie phenom, Francisco Liriano, 4–2. For the second year in a row, his win total did not match his performance, as he finished the season with a 7–6 record, a 2.30 ERA, and a 1.04 WHIP. However, Clemens averaged just under 6 innings in his starts and never pitched into the eighth.

Clemens has attracted controversy over the years for his outspoken comments, such as his complaints about having to carry his own luggage through an airport and his criticism of Fenway Park for being a subpar facility. On April 4, 2006, Clemens made an insulting remark when asked about the devotion of Japanese and South Korean fans during the World Baseball Classic: "None of the dry cleaners were open, they were all at the game, Japan and Korea". Toward the end of his career, his annual on-and-off "retirements" revived a reputation for diva-like behavior.

In October 2006, Clemens was named to Sports Illustrated's "all-time" team.

Clemens is a member of the Republican Party and donated money to Texas congressman Ted Poe during his 2006 campaign.

Debra posed in a bikini with her husband for a Sports Illustrated pictorial regarding athletes and their wives. This appeared in the annual Sports Illustrated Swimsuit Edition for 2003. Roger wore his Yankees uniform, with the jersey open. On February 27, 2006, to train for the World Baseball Classic, Roger pitched in an exhibition game between the Astros and his son's minor league team. In his first at-bat, Koby hit a home run off his father. In his next at-bat, Roger threw an inside pitch that almost hit Koby. Koby laughed in an interview after the game about the incident.

Clemens again decided to put off retirement before the 2005 season after the Houston Astros offered salary arbitration. The Astros submitted an offer of $13.5 million, and Clemens countered with a record $22 million demand. On January 21, 2005, both sides agreed on a one-year, $18,000,022 contract, thus avoiding arbitration. The deal gave Clemens the highest yearly salary earned by a pitcher in MLB history.

Clemens's 2005 season ended as one of the finest he had ever posted. His 1.87 ERA was the lowest in the major leagues, the lowest of his 22-season career, and the lowest by any National Leaguer since Greg Maddux in 1995. He finished with a 13–8 record, with his lower win total primarily due to the fact that he ranked near the bottom of the major leagues in run support. The Astros scored an average of only 3.5 runs per game in games in which he was the pitcher of record. The Astros were shut out nine times in Clemens' 32 starts, and failed to score in a 10th until after Clemens was out of the game. The Astros lost five of Clemens' starts by scores of 1–0. In April, Clemens did not allow a run in three consecutive starts. However, the Astros lost all three of those starts by a 1–0 score in extra innings.

Clemens won an emotional start on September 15, following his mother's death that morning. In his final start of the 2005 season, Clemens got his 4,500th strikeout. On October 9, 2005, Clemens made his first relief appearance since 1984, entering as a pinch hitter in the 15th, then pitching three innings to get win as the Astros defeated the Atlanta Braves in Game four of the National League Division Series. It is the longest postseason game in MLB history at eighteen innings. Clemens lasted only two innings in Game 1 of the 2005 World Series, and the Astros went on to be swept by the Chicago White Sox. It was the Astros' first World Series appearance. Clemens had aggravated a hamstring pull that had limited his performance since at least September.

By the end of the 2005 season, Clemens had won seven Cy Young Awards (he won the AL award in 1986, 1987, 1991, 1997, 1998, and 2001, and the National League award in 2004), an MVP and two pitching triple crowns. With his 2004 win, he joined Gaylord Perry, Randy Johnson, and Pedro Martínez as the only pitchers to win it in both leagues and became the oldest pitcher to ever win the Cy Young. He has also won the Sporting News Pitcher of the Year Award five times, was named an All-Star 11 times, and won the All-Star MVP in 1986.

Clemens came out of retirement, signing a one-year deal with his adopted hometown Houston Astros on January 12, 2004, joining close friend and former Yankees teammate Andy Pettitte. On May 5, 2004, Clemens recorded his 4,137th career strikeout to place him second on the all-time list behind Nolan Ryan. He was named the starter for the National League All-Star team but ultimately was the losing pitcher in that game after allowing six runs on five hits including a three run home run to Alfonso Soriano. Clemens finished the season with 4,317 career strikeouts, and his 18–4 record gave him a career record of 328–164. After the season he won his seventh Cy Young Award, extending his record number of awards, and also becoming the oldest player ever to win the Cy Young at age 42. This made him one of six pitchers to win the award in both leagues, joining Gaylord Perry, Pedro Martínez, and Randy Johnson and later joined by Roy Halladay and Max Scherzer.

Clemens was the losing pitcher for the Astros in game 7 of the 2004 NLCS against the St. Louis Cardinals, allowing 4 runs in 6 innings of work. Although he pitched well, he tired in the sixth inning, surrendering all four runs. In Game 4 of the 2005 NLDS against the Atlanta Braves, he made a dramatic emergency relief appearance, entering as a pinch-hitter (the first pinch-hitting appearance of his career), then pitching the 16th through 18th innings and collecting the series-ending win. However, during the World Series, a hamstring pull ended Clemens' start after two innings, as his hometown team lost to the eventual World Champion Chicago White Sox, 5–3. It was Clemens' only World Series appearance for the Astros. Clemens' overall postseason record with Houston was 4–2 with a 4.60 ERA, and 29 strikeouts and 15 walks in 41 innings. Clemens' total postseason record is 12–8 in 34 starts, with a 3.75 ERA with 173 strikeouts in 199 innings pitched. He pitched in six World Series, with a record of 3–0 in 8 starts, and a 2.37 ERA.

Debra once left a Red Sox game, when Clemens pitched for another team, in tears from the heckling she received. This is documented in an updated later edition to Dan Shaughnessy's best-selling book, Curse of the Bambino. Debra also was quoted in the book as stating that it was the poor attitude of Red Sox fans that prevented the team from ever winning the World Series (this was quoted prior to the Red Sox' 2004 World Series victory).

Early in 2003, Clemens announced his retirement, effective at the end of that season. On June 13, 2003, pitching against the St. Louis Cardinals in Yankee Stadium, Clemens recorded his 300th career win and 4,000th career strikeout, the only player in history to record both milestones in the same game. The 300th win came on his fourth try; the Yankee bullpen had blown his chance of a win in his previous two attempts. He became the 21st pitcher ever to record 300 wins and the third ever to record 4,000 strikeouts, joining Nolan Ryan (5,714) and Steve Carlton (4,136). Randy Johnson (4,875) has since also joined the 4,000 strikeout club. His career record upon reaching the milestones was 300–155; his record at the end of the season was 310–160 with 4,099 strikeouts. Clemens finished the season with a 17–9 record and a 3.91 ERA.

The end of Clemens's 2003 season became a series of public farewells met with appreciative cheering. His last games in each AL park were given extra attention, particularly his final regular season appearance in Fenway Park, when despite wearing the uniform of the hated arch rival, he was afforded a standing ovation by Red Sox fans as he left the field. (This spectacle was repeated when the Yankees ended up playing the Red Sox in the 2003 ALCS and Clemens got a second "final start" in his original stadium.) As part of a tradition of manager Joe Torre, Clemens was chosen to manage the Yankees' last game of the regular season. Clemens made one start in the World Series against the Florida Marlins; when he left trailing 3–1 after seven innings, the Marlins left their dugout to give him a standing ovation.

At Texas, Clemens pitched 35 consecutive scoreless innings, a NCAA record that stood until Justin Pope broke it in 2001.

In 2001, Clemens became the first pitcher in MLB history to start a season 20–1. He finished at 20–3 and won his sixth Cy Young Award. As of the 2018 season, he is the last Yankee pitcher to win the Cy Young Award. Clemens started for the Yankees in Game 7 of the 2001 World Series against the Arizona Diamondbacks, where he dueled Curt Schilling to a standstill after 6 innings, yielding only one run. The Diamondbacks went on to win the game in the 9th.

Clemens was traded to the New York Yankees before the 1999 season for David Wells, Homer Bush, and Graeme Lloyd. In 1999 and 2000, he won World Series titles with the Yankees. Since his longtime uniform number #21 was in use by teammate Paul O'Neill, Clemens initially wore #12, before switching mid-season to #22.

Clemens made an immediate impact on the Yankees' staff, anchoring the top of the rotation as the team went on to win a pair of World Series titles in 1999 and 2000. During the 1999 regular season, Clemens posted a 14–10 record with a 4.60 ERA. He logged a pair of wins in the postseason, where he pitched 7.2 innings of 1-run baseball during the Yankees' game 4 clincher over the Atlanta Braves. Clemens followed up 1999 with a strong 2000 season, in which he finished with a 13–8 record with a 3.70 ERA for the regular season. During the 2000 MLB postseason, he helped the Yankees win their third championship in as many years. He pitched a shutout against the Seattle Mariners in the ALCS that year and also pitched eight scoreless innings against the New York Mets in the World Series. Clemens set the ALCS record for strikeouts in a game when he fanned 15 batters in a one-hit shutout of the Mariners in Game 4 of the ALCS. A seventh inning lead-off double by Seattle's Al Martin was all that prevented Clemens from throwing what was, at the time, only the second no-hitter in postseason history (Yankee Don Larsen threw a perfect game against the Brooklyn Dodgers in Game 5 of the 1956 World Series and Roy Halladay would later throw a no-hitter in Game 1 of the 2010 National League Division Series). The Yankees won the 2000 World Series.

Clemens lost Game 3 of the 1999 ALCS in a matchup against Red Sox ace Pedro Martínez, which was the Yankees' only loss in the 1999 playoffs. His 3–0 record in the World Series includes a performance with New York down 2–0 in the 2001 series; then, in Game 7, it was Clemens who matched Curt Schilling; his start (6 innings, 1 run, 10 strikeouts) was forgotten in the wake of the Diamondbacks' famous ninth-inning comeback. In 2000, after losing two division series games to Oakland, Clemens pitched his most spectacular game as a Yankee in the ALCS against the Seattle Mariners: a complete game one-hit shutout with an ALCS-record 15 strikeouts. Clemens' overall postseason record with the Yankees is 7–4 with a 2.97 ERA, and 98 strikeouts and 35 walks in 102 innings. In the World Series, Clemens became the only pitcher to pitch against the Mets in a World Series while with both the Red Sox and the Yankees, having been with the Red Sox in 1986. Clemens started game three of the 2007 ALDS against the Cleveland Indians, but left in the third inning due to injury. He gave up three runs in only 2 ​⁄3 innings in what was to be his final appearance in the major leagues.

In 1999, while many of his performances and milestones were yet to come, he ranked number 53 on The Sporting News' list of the 100 Greatest Baseball Players, and was elected by the fans to the Major League Baseball All-Century Team. In 2005, the updated Sporting News list moved Clemens up to #15.

Jason Grimsley named Clemens, as well as Andy Pettitte, as a user of performance-enhancing drugs. According to a 20-page search warrant affidavit signed by IRS Special Agent Jeff Novitzky, Grimsley told investigators he obtained amphetamines, anabolic steroids and human growth hormone from someone recommended to him by former Yankees trainer Brian McNamee. McNamee was a personal strength coach for Clemens and Pettitte, hired by Clemens in 1998. At the time of the Grimsley revelations, McNamee denied knowledge of steroid use by Clemens and Pettitte. Despite initial media reports, the affidavit made no mention of Clemens or Pettitte.

However, Clemens's name was mentioned 82 times in the Mitchell Report on steroid use in baseball. In the report, McNamee stated that during the 1998, 2000, and 2001 baseball seasons, he injected Clemens with Winstrol. Clemens' attorney Rusty Hardin denied the claims, calling McNamee "a troubled and unreliable witness" who has changed his story five times in an attempt to avoid criminal prosecution. He noted that Clemens has never tested positive in a steroid test. Former U.S. Senator George Mitchell, who prepared the report, stated that he relayed the allegations to each athlete implicated in the report and gave them a chance to respond before his findings were published.

Clemens was dominant in his two seasons with the Blue Jays, winning the pitching Triple Crown and the Cy Young Award in both seasons (1997: 21-7 record, 2.05 ERA, and 292 strikeouts; 1998: 20-6 record, 2.65 ERA, and 271 strikeouts). After the 1998 season, Clemens asked to be traded, indicating that he did not believe the Blue Jays would be competitive enough the following year and that he was dedicated to winning a championship.

Clemens accomplished the 20-strikeout feat twice, the only player ever to do so. The second performance came more than 10 years later, on September 18, 1996 against the Detroit Tigers at Tiger Stadium. This second 20-K day occurred in his third-to-last game as a member of the Boston Red Sox. Later, the Tigers presented him with a baseball containing the autographs of each batter that had struck out (and those who had struck out more than once signed the appropriate number of times).

The Red Sox did not re-sign Clemens following the 1996 season, despite offering him "by far the most money ever offered to a player in the history of the Red Sox franchise." General Manager Dan Duquette remarked that he "hoped to keep him in Boston during the twilight of his career", but Clemens left and signed with the Toronto Blue Jays.

The emphasis on the misquoted 1996 "twilight" comment took on a life of its own following Clemens's post-Boston successes, and Duquette was vilified for letting the star pitcher go. Ultimately, Clemens would go on to have a record of 162–73 for the rest of his career after leaving the Red Sox.

Clemens recorded 192 wins for the Red Sox, tied with Cy Young for the franchise record and is their all-time strikeout leader with 2,590. No Red Sox player has worn his uniform #21 since Clemens left the team in 1996.

Clemens signed a four-year, $40 million deal with the Toronto Blue Jays after the 1996 season. In his first start in Fenway Park as a member of the Blue Jays, he pitched eight innings allowing only 4 hits and 1 earned run. 16 of his 24 outs were strikeouts, and every batter who faced him struck out at least once. As he left the field following his last inning of work, he stared up angrily towards the owner's box.

Clemens has been the focal point of several controversies. His reputation has always been that of a pitcher unafraid to throw close to batters. Clemens led his league in hit batsmen only once, in 1995, but he was among the leaders in several other seasons. This tendency was more pronounced during his earlier career and subsequently tapered off. After the 2000 ALCS game against the Mariners where he knocked down future teammate Alex Rodriguez and then argued with him, Seattle Mariners manager Lou Piniella called Clemens a "headhunter." His beaning earlier that year of Mike Piazza, followed by throwing a broken-bat in Piazza's direction in the 2000 World Series, cemented Clemens' surly, unapologetic image in the minds of many. In 2009, former manager Cito Gaston publicly denounced Clemens as a "double-talker" and "a complete asshole". Clemens was ranked 9th all-time in hit batsmen after the 2007 season.

He appeared in the 1994 movie Cobb as an unidentified pitcher for the Philadelphia A's. In 2003, he was part of an advertising campaign for Armour hot dogs with MLB players Ken Griffey Jr., Derek Jeter, and Sammy Sosa. Since 2005, Clemens has also appeared in many commercials for Texas-based supermarket chain H-E-B. In 2007, he appeared on a baseball-themed episode of MythBusters ("Baseball Myths"). He has also starred in a commercial for Cingular parodying his return from retirement. He was calling his wife, Debra Godfrey, and a dropped call resulted in his return to the Yankees.

Clemens greatest postseason failure came in the second inning of the final game of the 1990 ALCS against the Oakland Athletics, when he was ejected for arguing balls and strikes with umpire Terry Cooney, accentuating the A's four-game sweep of the Red Sox. He was suspended for the first five games of the 1991 season and fined $10,000. Clemens had two other playoff no-decisions, in 1988 and 1995, both occurring while Boston was being swept. Clemens' overall postseason record with Boston was 1–2 with a 3.88 ERA, and 45 strikeouts and 19 walks in 56 innings.

In 1991, Clemens captured his third Cy Young Award (finishing 2nd in the balloting in 1990 and 3rd in 1992) with an 18-10 record, 2.62 ERA, and 241 strikeouts. On June 21, 1989, Clemens surrendered the first of 609 home runs in the career of Sammy Sosa.

The Red Sox had a miserable 1987 season, finishing at 78-84, though Clemens won his second consecutive Cy Young Award with a 20-9 record, 2.97 ERA, 256 strikeouts, and seven shutouts. He was the first AL pitcher with back-to-back 20-win seasons since Tommy John won 20 with the Yankees in 1979 and '80. Boston rebounded with success in 1988 and 1990, clinching the AL East Division each year, but were swept by the Oakland Athletics in each ALCS matchup. Clemens led the American League in 1988 with 291 strikeouts and a career-high 8 shutouts. On September 10, 1988, Clemens threw a one-hitter against the Cleveland Indians at Fenway Park. Dave Clark's one-out single in the eighth inning was the only hit Clemens allowed in the game. In a 9-1 victory over Cleveland on April 13, 1989, Clemens recorded his 1,000 career strikeout by fanning Brook Jacoby with the bases loaded in the second inning.

He released an early autobiography, Rocket Man: The Roger Clemens Story written with Peter Gammons, in 1987. Clemens is also the spokesperson for Champion car dealerships in South Texas. In April 2009, Clemens was the subject of an unauthorized biography by Jeff Pearlman, titled The Rocket that Fell to Earth-Roger Clemens and the Rage for Baseball Immortality, that focused on his childhood and early career and accused Mike Piazza of using steroids. On May 12, Clemens broke a long silence to denounce a heavily researched expose by four investigative reporters from the New York Daily News, called American Icon: The Fall of Roger Clemens and the Rise of Steroids in America's Pastime. Clemens went on ESPN's Mike and Mike show to call the book "garbage", but a review by Michiko Kakutani of The New York Times called the book "gripping" and compared it to the work of Bob Woodward.

In 1986, Clemens won the American League MVP award, finishing with a 24-4 record, 2.48 ERA, and 238 strikeouts. Clemens started the 1986 All-Star Game in the Astrodome and was named the Most Valuable Player of the contest by throwing three perfect innings and striking out two. He also won the first of his seven Cy Young Awards. When Hank Aaron said that pitchers should not be eligible for the MVP, Clemens responded: "I wish he were still playing. I'd probably crack his head open to show him how valuable I was." Clemens was the only starting pitcher since Vida Blue in 1971 to win a league MVP award until Justin Verlander won the award in 2011.

On April 29, 1986, Clemens became the first pitcher in MLB history to strike out 20 batters in a nine-inning game, against the Seattle Mariners at Boston's Fenway Park. Following his performance, Clemens made the cover of Sports Illustrated which carried the headline "Lord of the K's [strikeouts]." Other than Clemens, only Kerry Wood and Max Scherzer have matched the total. (Randy Johnson fanned 20 batters in nine innings on May 8, 2001. However, as the game went into extra innings, it is not categorized as occurring in a nine-inning game. Tom Cheney holds the record for any game: 21 strikeouts in 16 innings.) Clemens attributes his switch from what he calls a "thrower" to a "pitcher" to the partial season Hall of Fame pitcher Tom Seaver spent with the Red Sox in 1986.

In the 1986 American League Championship Series, Clemens pitched poorly in the opening game, watched the Boston bullpen blow his 3–1 lead in the bottom of the ninth inning of Game 4, and then pitched a strong Game 7 to wrap up the series for Boston. The 1986 ALCS clincher was Clemens' first postseason career victory. He did not win his second until 13 years later.

After a bad start in Game 2 of the 1986 World Series (which the Red Sox won 9–3), Clemens returned to the mound for Game 6, which would have clinched the World Series for the Boston Red Sox. Clemens left the game after 7 innings leading 3–2, but the Red Sox went on to lose the game in the 10th inning, and subsequently, the championship. Clemens' departure was highly debated and remains a bone of contention among the participants. Red Sox manager John McNamara claimed Clemens took himself out due to a blister, though Clemens strongly denies that.

Clemens debuted in the MLB in 1984 with the Red Sox, whose pitching staff he anchored for 12 years. In 1986, he won the American League (AL) Cy Young Award, the AL Most Valuable Player (MVP) Award, and the All-Star Game MVP Award, and he struck out an MLB-record 20 batters in a single game (Clemens repeated the 20-strikeout feat 10 years later). After the 1996 season, Clemens left Boston via free agency and joined the Toronto Blue Jays. In each of his two seasons with Toronto, Clemens won a Cy Young Award, as well as the pitching triple crown by leading the league in wins, ERA, and strikeouts. Prior to the 1999 season, Clemens was traded to the Yankees where he won his two World Series titles. In 2001, Clemens became the first pitcher in major league history to start a season with a win-loss record of 20–1. In 2003, he reached his 300th win and 4,000th strikeout in the same game. Clemens left for the Houston Astros in 2004, where he spent three seasons and won his seventh Cy Young Award. He rejoined the Yankees in 2007 for one last season before retiring. He is the only pitcher in major league history to record over 350 wins and strike out over 4,500 batters.

Clemens was selected in the first round (19th overall) of the 1983 MLB draft by the Boston Red Sox and quickly rose through the minor league system, making his MLB debut on May 15, 1984. An undiagnosed torn labrum threatened to end his career early; he would successfully undergo arthroscopic surgery at the hands of the then relatively unknown Dr. James Andrews.

He began his college career pitching for San Jacinto College North in 1981, where he was 9–2. The New York Mets selected Clemens in the 12th round of the 1981 Major League Baseball draft, but he did not sign. He then attended the University of Texas at Austin, compiling a 25–7 record in two All-American seasons, and was on the mound when the Longhorns won the 1983 College World Series. He became the first player to have his baseball uniform number retired at the University of Texas. In 2004, the Rotary Smith Award, given to America's best college baseball player, was changed to the Roger Clemens Award, honoring the best pitcher.

Clemens married Debra Lynn Godfrey (born May 27, 1963) on November 24, 1984. The couple has four sons: Koby Aaron, Kory Allen, Kacy Austin, and Kody Alec—all given "K" names to honor Clemens's strikeouts ("K's"). Koby was at one time a minor league prospect in various MLB clubs. Kacy played college baseball for the Texas Longhorns, and was drafted by the Blue Jays in the eighth round of the 2017 Major League Baseball draft. Kody also played college baseball for the Texas Longhorns, and was drafted 79th overall by the Detroit Tigers in the third round of the 2018 Major League Baseball draft.

William Roger Clemens (born August 4, 1962), nicknamed "Rocket", is an American former professional baseball pitcher who played 24 seasons in Major League Baseball (MLB) for four teams, most notably the Boston Red Sox and the New York Yankees. Clemens was one of the most dominant pitchers in major league history, tallying 354 wins, a 3.12 earned run average (ERA), and 4,672 strikeouts, the third-most all time. An 11-time All-Star and two-time World Series champion, he won seven Cy Young Awards during his career, more than any other pitcher in history. Clemens was known for his fierce competitive nature and hard-throwing pitching style, which he used to intimidate batters.

Clemens was born in Dayton, Ohio, the fifth child of Bill and Bess (Lee) Clemens. He is of German descent, his great-grandfather Joseph Clemens having immigrated in the 1880s. Clemens's parents separated when he was an infant. His mother soon married Woody Booher, whom Clemens considers his father. Booher died when Clemens was nine years old, and Clemens has said that the only time he ever felt envious of other players was when he saw them in the clubhouse with their fathers. Clemens lived in Vandalia, Ohio, until 1977, and then spent most of his high school years in Houston, Texas. At Spring Woods High School, Clemens played baseball for longtime head coach Charles Maiorana and also played football and basketball. He was scouted by the Philadelphia Phillies and Minnesota Twins during his senior year, but opted to go to college.