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.