1999 Winnipeg Blue Bombers

The 1999 Winnipeg Blue Bombers finished in 4th place in the East division with a 6–12 record and failed to make the playoffs.

1999 CFL All-Stars

 * LB – Maurice Kelley, CFL All-Star

Eastern All-Star Selections

 * SB – Milt Stegall, CFL Eastern All-Star
 * WR – Robert Gordon, CFL Eastern All-Star
 * ST – Wade Miller, CFL Eastern All-Star
 * LB – Maurice Kelley, CFL Eastern All-Star