O'Leary-Orange was drafted in the fourth round, 37th overall, by the Winnipeg Blue Bombers in the 2020 CFL Draft, but did not play in 2020 due to the cancellation of the 2020 CFL season.[3][4] He then signed with the team on April 26, 2021.[4] He began the 2021 season on the practice roster, but was elevated to the active roster in week 14 where he played in his first professional game on November 6, 2021, against the Montreal Alouettes.[5] He dressed in the last three regular season games as a backup receiver where he recorded two special teams tackles.[6] He also played in both post-season games that year and won his first Grey Cup championship after the Blue Bombers defeated the Hamilton Tiger-Cats in the 108th Grey Cup championship game.[5]