The Winnipeg Blue Bombers moved up in the CFL draft without even making a trade. The Bombers moved into the sixth spot in the CFL's college entry draft when the Montreal Alouettes lost their first choice. The Alouettes lost the choice because the club exceeded its salary cap by more than $100,000.
On May 20, the Bombers officially signed former U.S. college stars Bryan Randall and Cleveland McCoy.
On Tuesday, May 27, Milt Stegall announced that he will not participate in the Winnipeg Blue Bombers training camp after undergoing knee surgery May 2.
The Bombers also announced they've released veteran cornerback Juran Bolden. The 33-year-old Tampa native spent the 2007 CFL season with Winnipeg, but didn't play in the Grey Cup due to a hamstring injury. The six-foot-three, 210-pound Bolden was originally a fourth-round pick of the NFL's Atlanta Falcons in 1996. Bolden twice played for the Falcons ('96–'97, 2002–'03). Other NFL teams included the Carolina Panthers ('98), Kansas City Chiefs ('99), Jacksonville Jaguars ('04) and Tampa Bay Buccaneers ('05–'06).
On September 12 at Rogers Centre, Milt Stegall became the most prolific receiver in the history of the CFL. The slotback caught a 92-yard pass at 9:02 in the second quarter to raise his career total to 14,983, breaking the mark of 14,891 yards previously held by former Stampeders receiver Allen Pitts. Stegall took a pass from Kevin Glenn and scored a touchdown, his second of the game. It put the Bombers ahead 28–3. The touchdown was Stegall's 14,983rd career receiving yard. With the record broken, the announced crowd of 28,453 stood to applaud the milestone.
September 9: Winnipeg acquired middle linebacker Zeke (And Destroy) Moreno and a conditional draft pick from Hamilton for its first-round draft pick in 2009 and the rights to Canadian defensive lineman Corey Mace.