[5] Bennett committed to the Oregon Ducks on June 18, 2009[6] where he played for two years, until he transferred to Southeastern Louisiana.

[7] [8] Bennett signed with the Indianapolis Colts as an undrafted free agent on May 4, 2015 [9] until he was released during final roster cuts on September 5, 2015.

[13] Bennet was released by the Roughriders on June 17, 2017, as the team trimmed its roster down for the start of the season.

[14] Bennett returned to the Winnipeg Blue Bombers when he signed with the team on May 24, 2018, at the start of training camp.

[16] He dressed in 17 regular season games as the short-yardage quarterback, attempting no passes, but rushed the ball 16 times for 69 yards and one touchdown.