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On May 9, 2019, Anderson announced his retirement from the NFL. He later attributed his retirement to lingering effects from the 2018 concussion; he remains in regular contact with Allen and approved of the hiring of his (Anderson's) friend Ken Dorsey as quarterbacks coach.

In Week 4 of the 2016 season against the Atlanta Falcons, Anderson entered the game after an injury to Newton and threw for 172 yards, two touchdowns, and two interceptions as the Panthers lost by a score of 48–33. Due to Newton's injury, Anderson started the Week 5 game against the Buccaneers and threw for 278 yards and two interceptions as the Panthers lost by a score of 17–14. In Week 13 against the Seattle Seahawks, Anderson made his second start of the season. He threw an interception on the Panthers first play on offense and was then replaced by Newton. Anderson started the game due to Newton having violated the team's dress code. Anderson came into the 2017 NFC Wild Card Round on January 7, 2018 against the New Orleans Saints in the fourth quarter after Newton went down with an injury. He had one pass attempt in the 31-26 defeat.

On October 7, 2018, it was announced Anderson would sign with the Buffalo Bills, reuniting with Sean McDermott and Brandon Beane from his days playing for the Carolina Panthers, to serve as backup and mentor to rookie quarterback Josh Allen. The Bills completed the transaction on October 9.

On December 31, 2018, Anderson signed a one-year contract extension with the Bills.

On February 7, 2016, Anderson was part of the Panthers team that played in Super Bowl 50. In the game, Anderson served as Cam Newton's active-backup as the Panthers fell to the Denver Broncos by a score of 24–10.

On September 7, 2014, Anderson made his first start since 2010 after Newton suffered an injury which held him out. In the game, Anderson completed 24 of 34 passes for 230 yards, two touchdowns, and no interceptions, leading the Panthers to a 20–14 victory over the Tampa Bay Buccaneers. Anderson would have his second start of the season after Newton was involved in a car accident, coincidentally also against the Buccaneers. Anderson finished the game by completing 25 of 40 passes for 277 yards, a touchdown, and no interceptions, helping the Panthers win 19–17.

Anderson's early entry into the starting role came on the heels of Oregon State's most successful period to date. Capped by a Fiesta Bowl win over Notre Dame, the team went 11–1 in 2000 and ranked 4th in the nation under head coach Dennis Erickson. Following such a successful season, expectations were exceptionally high in 2002 for both Anderson and the OSU program.

Despite this, Anderson helped the Beavers record an 8–5 season. His work was good enough to give them entry into the 2002 Insight Bowl, against the University of Pittsburgh. Anderson's team lost 38–13 and coach Erickson left for a National Football League head coaching position with the San Francisco 49ers.

Pressures on the entire team to keep the program on-track were compounded by the coaching change. The return of previous head coach Mike Riley from the NFL meant learning an entirely new system. With help from teammate and star running back Steven Jackson, Anderson again rose to the occasion and played a leading role in propelling the team to an 8–5 record, this time ending the 2003 season with a 55–14 Las Vegas Bowl win over a then up-and-coming New Mexico program.

Another close game that could have put the Browns in the playoffs was December 23 against the Bengals, in which the Browns went scoreless in the first half, but held the Bengals scoreless in the second half. Anderson had four interceptions, two of them on consecutive plays, and one more in the Cincinnati end zone as Cleveland appeared to be heading for a scoring drive. The Browns also had two turnover-on-downs possessions. Anderson threw two touchdown passes to Braylon Edwards, Cleveland's only scores in the game. The game ended in a 19–14 loss.

Anderson led the Browns to a 10–6 overall record, 10–5 in games in which he started. Anderson finished with 29 touchdowns to 19 interceptions. During the week of December 12–18, Anderson was named as a first alternate for the 2008 Pro Bowl at quarterback. On February 4, Tom Brady announced he would not be attending the Pro Bowl due to injury. This paved the way for Anderson to make his first and only appearance in the Pro Bowl.

On October 17, following an injury to Allen and a poor performance by backup quarterback Nathan Peterman in relief, Anderson was named the Week 7 starter for the Bills against the Indianapolis Colts. During the game, Anderson threw for 175 yards, no touchdowns, and three interceptions in a 37–5 loss. With Allen still injured, Anderson made the start the following week against the New England Patriots on Monday Night Football. He threw for 290 yards, no touchdowns, and one interception before leaving the game in the fourth quarter. He was put into concussion protocol and ruled out for the Week 9 game against the Chicago Bears, and Peterman was named the starter once again.

Anderson signed with the Carolina Panthers on July 31, 2011. He served as the backup to quarterback Cam Newton and played only a few times for Carolina either to end the game or play for an injured Newton.

On March 17, 2010, Anderson signed a two-year deal worth $7.25 million with the Arizona Cardinals. After Kurt Warner retired and Matt Leinart was released, Anderson became the starting quarterback for the Cardinals. After struggling in his first few games, Anderson was benched in favor of rookie Max Hall on October 6. Anderson was named the starting quarterback again for the November 7 game against the Minnesota Vikings after Hall struggled. However, in week 14 he was benched again after suffering a concussion and was replaced with Hall, whose season ended with a separated shoulder later in the game. Rookie John Skelton finished the game and succeeded Anderson as the Cardinals' starting quarterback. Anderson also created a notable soundbite after being caught on national TV laughing with teammate Deuce Lutui while he and his team were playing poorly. His subsequent anger toward the reporter who kept questioning him on the subject made national news and was featured on several sports shows. Anderson was released by the Cardinals on July 28, 2011.

In the 2009 season, Anderson continued to compete with Quinn. He appeared in eight games for the Browns. He finished with 888 passing yards, three touchdowns, and ten interceptions. The Browns finished the season with a 5–11 record.

On February 29, 2008, the first day of free agency, after speculation that Anderson would leave Cleveland to pursue a bigger contract, Anderson agreed to a three-year contract to stay with the Browns through the 2010 season. With fans split between the proven Anderson and the locally-homegrown Quinn (an image of Quinn wearing a Bernie Kosar jersey as a kid was shown at the 2007 NFL Draft), many were speculating if the Browns were in a similar position the San Diego Chargers were in a few years back with Drew Brees and their first-round pick Philip Rivers.

The 2008 season was a tough one for the Browns and Anderson. In the preseason, he suffered a concussion when he was sacked by Osi Umenyiora of the New York Giants. This would prevent him from practicing for the majority of the preseason. In the season opener against the Dallas Cowboys, he was 11-of-24 for 110 yards and a touchdown. On November 3, after starting out the season the Browns announced that Anderson would be benched in favor of Quinn. On November 23, during a game against the Houston Texans, Quinn was benched by Crennel in favor of Anderson. On November 25, Quinn was ruled out for the remainder of the season with a broken finger and Anderson was renamed the starting quarterback. On November 30, Anderson was injured during a game versus the Indianapolis Colts. It was later revealed to be an MCL injury, which put Anderson out for the season. Ken Dorsey came into the starting role, but could not save the Browns. The Browns lost the last four games to finish with a 4–12 record.

Although some reports said he outplayed incumbent starter Frye and rookie Brady Quinn in minicamp, Anderson was not as productive in the pre-season games and Frye was named the starter for the 2007 season. Head coach Romeo Crennel earlier said that the two were so close in effectiveness that he would use a coin toss to decide which quarterback would start the first preseason game. Anderson would take over for Frye in the 2007 opener after Frye was ineffective in the first quarter against the Browns' archrival, the Pittsburgh Steelers. The game was Frye's last in a Browns uniform, as he was traded to the Seattle Seahawks for a sixth-round draft pick two days later. Named the starting quarterback by Crennel for Week 2, Anderson threw for 328 yards and five touchdowns against the Cincinnati Bengals in his first start. His passer rating for the game was 121.0 as the Browns defeated the Bengals 51–45, solidifying Anderson's role. In the same game, Bengals quarterback Carson Palmer threw for six touchdown passes. It was only the third time in NFL history that two quarterbacks had thrown at least five touchdown passes in the same game.

In Week 13 of the 2007 season, the Browns faced the Arizona Cardinals. Down 27–21 late in the 4th, the Browns drove down to the Cardinals 34-yard line. On fourth down, Anderson threw a pass to the end zone which was caught by Kellen Winslow. The pass was ruled out of bounds and held up through review. Anderson argued that Winslow was forced out, but the force-out rule was not reviewable. The game was notable for the officials’ missed call of a Braylon Edwards catch and tackle by contact, but mistakenly ruled a touchdown as Edwards got up and ran to the endzone.

Anderson served as Frye's backup for the Cleveland Browns in 2006 season. He made his NFL debut against the Denver Broncos at Cleveland Browns Stadium, on October 22, taking one snap after Frye was briefly shaken up. His second NFL appearance was more noteworthy. After Frye injured his wrist during the first half of Cleveland's December 3 game against the Kansas City Chiefs, Anderson played the entire second half. He threw his first two NFL touchdowns in that game, connecting with tight end Steve Heiden twice in the fourth quarter. Anderson scrambled for 33 yards in overtime, moving the ball from the Kansas City 45-yard line to the 12-yard line, after which the Browns were in field goal range. His play was instrumental in leading the Browns back from a 28–14 deficit to a 31–28 overtime victory. Overall, Anderson appeared in five games and recorded 793 passing yards, five touchdowns, and eight interceptions in the 2006 season.

Anderson was selected out of Oregon State University by the Baltimore Ravens in the sixth round of the 2005 NFL Draft (213th overall), but never played for them and was waived on September 20, 2005.

Throughout the 2004 season, Anderson successfully branched out and surprised many defenses with his ability to escape the tackle and run the ball effectively. Although the team's 7–5 performance was far from spectacular, Anderson became nationally recognized as a dangerous offensive weapon who could strike long gains at will. The Beavers went without Steven Jackson through the 2004 season (Jackson was drafted into the NFL at the end of the 2003 season). Even without the star running back, Anderson led his team back into the Insight Bowl where they again faced Notre Dame (led by future Browns teammate Brady Quinn). The Beavers never trailed in the game and defeated the Irish 38–21. Anderson passed for 359 yards and had four touchdown passes with no interceptions.

Anderson is the fourth player in Pac-10 history to throw for over 4,000 yards in a single season, setting an Oregon State Beavers football record at 4,058 yards in the 2003 season. He ranks second in the Pac-10 for career touchdown passes, at 79 (also an Oregon State record). He is the 6th person to ever throw for 10,000 yards in a career in the Pac-10.

At the start of his sophomore year (2002), Anderson was thrust into the starting role as a quarterback and handed the reins of a rapidly improving program. Despite an early string of losses, Oregon State had no serious competition for quarterback in 2002 and his job was secure.

As a freshman in the 2001 season, Anderson appeared in five games and recorded 263 passing yards, one touchdown, and three interceptions.

On September 30, Anderson beat the team that drafted him, the Baltimore Ravens. He threw for two touchdowns and 204 yards, completing 10 of 18 pass attempts with just one interception. The Browns would later beat the Ravens again, making it the first time since 2001 that the Browns were able to sweep the Ravens.

Anderson grew up in Scappoose, Oregon, where he led the Scappoose Indians football team to one of their record three consecutive state football championships in Class 3A football. He excelled at basketball and was named state player of the year in both football and basketball his senior year. He participated in the first ever U.S. Army All-American Bowl game in 2000. He was a childhood friend and schoolmate of Playboy Playmate Sara Jean Underwood.

Derek Matthew Anderson (born June 15, 1983) is a former American football quarterback who played 14 seasons in the National Football League (NFL). He was drafted by the Baltimore Ravens in the sixth round of the 2005 NFL Draft. He played college football at Oregon State. A 2007 Pro Bowler, Anderson has also played for the Cleveland Browns, Arizona Cardinals Carolina Panthers, and the Buffalo Bills.