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On June 12, 2019, his 40th birthday, Glenn retired from his playing career.

On January 15, 2018, the Edmonton Eskimos announced that they had signed Glenn to a one-year contract. Glenn's rights have now been held by every team in the Canadian Football League. On September 29, 2018, while serving as the backup quarterback to Mike Reilly, Glenn dressed for his 300 CFL game; trailing only Damon Allen (370) and Anthony Calvillo (329) for most games dressed by a quarterback.

With the potential revival of the Atlantic Schooners as the 10th CFL team, Glenn has joked that he may want to come out of retirement to sign a one-day contract with them to continue to hold on to his unique claim of having been part of every CFL team. In a straw poll, Schooner fans (in advance of the teams 2018 revival announcement prior to the 106th Grey Cup) said that they would want Glenn as a QB selection in an expansion draft if the team's revival comes to fruition. Mid-way through the 2019 season the Blue Bombers (7–2 at the time) reached out to Glenn to see if he was interested in coming out of retirement following an injury to starting quarterback Matt Nichols; however, Glenn declined the offer although he did consider it "very tempting".

On January 23, 2017, Glenn signed a contract with the Saskatchewan Roughriders. During training camp and preseason Glenn beat out Canadian quarterback Brandon Bridge, second year quarterback Bryan Bennett and former NFL quarterback Vince Young for the starting job: The latter two were released before the start of the season. Glenn was the Riders starting quarterback for most of the 2017 season, however in the last third of the season he began splitting snaps with Brandon Bridge. In early August Glenn surpassed Ron Lancaster moving into sixth place on the CFL's all-time passing yards list. On September 29, 2017, in his 197th game as a starting quarterback, Glenn recorded his 100th win (tying Matt Dunigan for the eight most all-time). Overall Glenn had a solid season for the Riders, leading the team to a 10-8 record and qualifying for the East division playoff via crossover. On January 3, 2018 the Riders acquired quarterback Zach Collaros, the following day they announced they had released Kevin Glenn.

Glenn began the 2016 season as the starting quarterback on a crowded depth chart that included the likes of; Rakeem Cato, Vernon Adams, Brandon Bridge and Jonathan Crompton. Glenn started the first two games of the season of the Alouettes, had a bye for the third week and missed the fourth week with an eye infection. Glenn started nine of the team's first ten games of the season, but only managed to win three of them. As a result, head coach Jim Popp announced Rakeem Cato would be the starting quarterback in Week 12, relegating Glenn to the backup role.

On September 11, 2016, Glenn was traded to the Winnipeg Blue Bombers to serve as the back-up for Matt Nichols. He dressed for seven games for the Bombers while playing in one, completing two of his four pass attempts for 16 yards. Unable to come to terms on a new contract, the Bombers released Glenn about a month before he was set to become a free agent.

On February 19, 2015, Glenn signed with the Saskatchewan Roughriders, returning him to the team where he began his professional career. Glenn was the backup quarterback on the depth chart and saw action in the first game of the season, when starting quarterback Darian Durant suffered a leg injury. It was revealed after the game that Durant had suffered a torn Achilles tendon, ending his season and making Glenn the starter. Glenn learned Chapdelaine's offensive scheme quickly and excelled, making Saskatchewan's offense the best in the league though the first four games of the season (all losses). Glenn played in 9 games for the Riders but the team struggled and quickly fell out of playoff contention.

On trade deadline day for the 2015 season (October 14, 2015), Glenn was traded by the Roughriders to the Montreal Alouettes, in exchange for a fifth-round pick in the 2016 CFL Draft. At the time of the trade, the Alouettes had a record of 5-9 tying them for the crossover playoff spot; whereas the Roughriders season was over after they had been officially eliminated from post-season contention. Glenn played in three of the final four games for the Alouettes to close out the season, however, he was not able to earn Montreal a playoff berth, losing the crossover to the BC Lions.

On May 13, 2014, Glenn was traded to the BC Lions during the 2014 CFL Draft in exchange for the fifth overall pick in that draft. With Travis Lulay suffering a major injury, Kevin Glenn started in 17 of the 18 regular season games, and also in the Eastern Semi-Final. Based on QB passer rating statistic, the 2014 season was Glenn's worst passing season since his 2008 campaign with the Blue Bombers. The Lions finished the season fourth in the West Division, but qualified for the playoffs by virtue of the "crossover" rule and the fact their 9-9 record was marginally better than the 3rd-best team in the East. The Lions lost the East Division Semi-Final by a score of 50-17 and head coach Mike Benevides was fired less than a week later despite having had his contract extended to 2016. Glenn was not re-signed by the Lions and became a free agent on February 10, 2015.

Glenn returned to the Stamps for the 2013 CFL season once again as a back up to Drew Tate. In similar fashion to the previous year Glenn came in relief of an injured Tate in Week 2 and was named the starter for Week 3 against the Alouettes due to Tate's injury. Kevin Glenn started in Week 3 and 4 against the Montreal Alouettes, however, he was unable to finish the Week 4 game due to sustaining an elbow injury in the 3rd-quarter, sustained while taking a hit completing a 45-yard pass to Marquay McDaniel. On October 18, 2013, Glenn passed Tom Clements to become the 10th all-time leading quarterback in terms of passing yards. Glenn played a total of 15 of the 18 regular season games in 2013, leading the Stamps to a league best record of 14-4, earning a first round bye. In the West-Final Glenn was pulled after the first half after struggling against the Roughriders. The Stamps lost the game, ending their season.

On December 16, 2013, Glenn was drafted by the Ottawa Redblacks in the 2013 CFL Expansion Draft. Prior to the start of CFL free agency, the RedBlacks signed Henry Burris and named him the starter, leaving Glenn once again relegated to a backup role. On March 6, 2014, Glenn announced that he had requested to be traded, something he had discussed with the RedBlacks front office since the signing of Burris on February 4. Ottawa GM Marcel Desjardins had said that he would not release Glenn.

On January 3, 2012, Glenn was traded to the Calgary Stampeders along with Mark Dewit and a conditional draft pick for Henry Burris. Glenn was brought in by the Stamps to serve as a backup for starter Drew Tate. When Tate went down with a major injury in week 2 Glenn became the starter. Kevin Glenn went on to start the next 15 games for the Stampeders, winning 10 of them. His 67.9 percent completion rate during the 2012 campaign was the best of his career to that point. Tate returned from injury and went back to starting status for the final two games of the regular season and the Western Division Semi-Finals. When Tate sustained a different injury in the Western Semi-Final, Glenn became the starter for the remainder of the 2012 playoffs. Glenn led the Stamps to victory over the BC Lions in the Western Final, but was unable to defeat the Toronto Argonauts in the 100th Grey Cup, losing 35-22. During the 2012 season, Glenn passed Dieter Brock on the CFL's all time passing yardage chart, surpassing Brock's total of 35,025 yards.

After a very strong year in 2010, Glenn saw his production decrease in 2011, throwing the same number of interceptions (17), but 13 fewer touchdowns. Head coach Marcel Bellefeuille elected to use a two-quarterback system for portions of the season which had Glenn sharing snaps with Quinton Porter. However, Glenn managed to lead the Hamilton Tiger-Cats to the playoffs for the third consecutive season with a record of 8-10 by starting 17 regular season games.

The 2008 Winnipeg Blue Bombers season started out poorly for Glenn with 976 yards, 2 touchdowns, 8 interceptions, a QB Rating of only 65.9, and 4 losses in 4 starts. He then lost his job to Ryan Dinwiddie who guided the team to their first win. After Dinwiddie led the team to its first win he started struggling and lost his next game and Glenn was given his job back. Glenn and the Bombers became the first team in CFL history to host and lose a playoff-crossover match. In the off-season quarterback Stefan LeFors was traded by Edmonton to Winnipeg in exchange for draft picks. Glenn was subsequently released on March 9, 2009.

Glenn signed with the Hamilton Tiger-Cats on March 20, 2009. He began the 2009 season as the backup to Quinton Porter, but after Porter struggled during the season, Glenn took over as the starting quarterback. Glenn led the Ti-Cats to their first postseason appearance since 2004 with a record of 9-9. Hamilton was eliminated in overtime in the first round by the crossover BC Lions. In his second year as the starter Glenn led the Tiger-Cats to another 9-9 season this time to lose to the Toronto Argonauts in the first round.

Glenn emerged as one of the CFL's elite quarterbacks during the 2007 season. By week 7, Glenn had the league's best quarterback rating (107.3), and had thrown for 2078 yards and 11 touchdowns (with only 3 interceptions). However, by the end of the 2007 season, Glenn's quarterback rating had fallen to 93.2, making him 5th amongst starting quarterbacks, in the 8 team CFL. Glenn led Winnipeg to the 95th Grey Cup with a win in the East Division final defeating Toronto 19–9 before leaving the game due to a broken arm and causing him to miss the Grey Cup game, which the Bombers would ultimately lose.

The 2006 season was a year of great growth for Kevin. Though working in a brand new offensive system under new head coach Doug Berry, Glenn performed admirably. In a Week 8 game, Glenn slightly tore his ACL, but returned to the field to play his former team the Saskatchewan Roughriders in their Labour Day tilt. Glenn managed to lead the Bombers to their first playoff appearance in two years.

The 2005 season was more successful for Glenn. Despite missing three games due to injury, Glenn had his best season as a Bomber. He completed 231 of 403 pass attempts (57.3 per cent) for 3,571 yards and 27 touchdowns. His 27 TD passes was third best in the CFL. He also rushed for one touchdown on October 10 versus the B.C. Lions. That October 10 game at Canad Inns Stadium was arguably Glenn's best single-game performance of his CFL career. He passed for 410 yards and five touchdowns, including four TD completions to slotback Milt Stegall. Glenn would go on to surpass the 300-yard passing mark on five occasions in 2005. Despite impressive numbers from Glenn the Bombers finished 5-13.

On May 19, 2004, the Roughriders traded Glenn to the Toronto Argonauts for their best selection (third overall) in the 2005 CFL Draft, however later in the day, Glenn was traded to the Winnipeg Blue Bombers for their best selection in that draft (also the third overall selection).

In the 2004 season, Glenn played back-up to Khari Jones until Jones was traded mid-season. In 8 games that season Glenn passed for 2,329 yards on 274 attempts and 166 completions for an average of 14 yards. He also had 14 touchdown passes and eight interceptions. Glenn also rushed 30 times for 125 yards and two touchdowns. That season the Bombers finished with a disappointing record of 7-11, missing the playoffs

Glenn entered free agency on February 17, 2003, but re-signed with the Roughriders on March 21, 2003. He dressed for all 18 regular-season games in the 2003 season plus the 2003 West Division Semifinal and the 2003 West Division Final. Glenn completed 40-of-his-73 pass attempts (54.8 per cent) for 508 yards, one touchdown and four interceptions. He also rushed 13 times for 48 yards and a 3.7-yard average.

Glenn played in 11 regular-season games in the 2002 season as well as the 2002 East Division Semifinal. He started three games on the season. He completed 60-of-95 passes (63.2%) for 777 yards, three touchdowns and three interceptions. He rushed 21 times for 83 yards and one touchdown.

Glenn originally signed with the Saskatchewan Roughriders on June 8, 2001. He appeared in 18 regular-season games for Saskatchewan in the 2001 season; starting for six of those games. Glenn completed 70-of-154 pass attempts (45.5 percent) for 938 yards, two touchdowns and nine interceptions. He recorded 28 carries for 152 yards (5.4-yard average) and two touchdowns.

Glenn played college football for the Illinois State Redbirds, where he set 25 school records during his four years there. He completed 645 of 1,119 pass attempts (57.6 percent) for 8,032 yards and 61 touchdowns, and also rushed 247 times for 490 yards and eight scores during his college career. He once tossed 101 straight passes without an interception and, in 1998, he led the Gateway Football Conference in passing yards per game, passer efficiency, and total offence. Glenn led Illinois State to its first playoff appearance in 1998.

Kevin Glenn, Jr. (born June 12, 1979) is a former American professional Canadian football quarterback. He was originally signed by the Saskatchewan Roughriders of the Canadian Football League (CFL) as an undrafted free agent in 2001. He played college football for the Illinois State Redbirds and high school football at Detroit St. Martin de Porres. Glenn is a journeyman quarterback who is the only player to ever have had his rights held by every team in the CFL.