O'Connor received several scholarship offers to play football and was named ESPN's sixth-ranked quarterback in the 2014 recruiting class. He ultimately chose Pennsylvania State University to play for then-head coach, Bill O'Brien, and the Nittany Lions. O'Brien had resigned to accept a position as the Houston Texans' head coach, but O'Connor elected to continue with his decision to enroll at Penn State anyway. He redshirted during his first season there behind the incumbent starter, Christian Hackenberg. Near the end of the 2014 season, O'Connor announced his intention to transfer schools.
UBC
On February 12, 2015, it was formally announced that O'Connor had committed to play for Blake Nill and the UBC Thunderbirds. As a freshman starter, he had immediate success, starting in all eight games, posting 165 completions on 276 pass attempts for 2383 yards, 13 touchdowns, and five interceptions to lead UBC to a 6-2 regular season record. He led the team to a perfect 4-0 record in the post-season, including UBC's 51st Vanier Cup championship win where he was named the game's most valuable player. The Thunderbirds qualified for the playoffs in each of the four seasons that O'Connor was the team's starting quarterback. He finished his collegiate career having played in 32 regular season games, completing 773 passes out of 1197 attempts for 9990 yards, 61 touchdowns, and 22 interceptions.
Professional career
Attracting the attention of professional leagues, O'Connor was ranked as the 17th best prospect in the Canadian Football League's Central Scouting Bureau Final Rankings. Consequently, he was drafted in the third round, 20th overall, in the 2019 CFL Draft by the Toronto Argonauts and signed with the team on May 17, 2019. He began the 2019 season on the Argonauts' injured list, but dressed in his first professional game on July 6, 2019 against the BC Lions. With Argonauts eliminated from the playoffs, O'Connor took his first regular season snaps under centre on October 26, 2019 against his hometown Ottawa Redblacks. In that game, he threw his first career touchdown pass; an 11-yard completion to Rodney Smith. Smith had thrown the ball into the stands, but the fan who retrieved it threw the keepsake back to Argos staff members. O'Connor dressed for 9 games his rookie season, and saw snaps in two. He completed 15 passes out of 25 attempts for 173 yards and a touchdown.
