	Whitehead signed with the Winnipeg Blue Bombers of the Canadian Football League (CFL) on May 9, 2019. He had a breakout performance in Week 3 of the 2019 regular season, catching 7 passes for 155 yards with two touchdowns. Whitehead finished the year with 52 catches for 521 yards and two touchdowns, one rushing touchdown, and one kickoff return for a score. 