Pipkin played quarterback for Tiffin University from 2014–2016. As a freshman in 2014, Pipkin completed 33 out of 54 pass attempts for 231-yards and one touchdown with three interceptions. In 2015, Pipkin became the Dragon's starting quarterback and finished the season with 250 completions out of 390 attempts for a career-high 3,227 passing yards and 32 touchdown and six interceptions in 11 games and 11 starts. He returned for his junior season in 2016 and completed 216 passes, out of 333 pass attempts for 2,534 passing yards. Pipkin also had 25 touchdown passes and six interceptions in 11 games and 11 starts. He finished his college career with a total of 499 pass completions, 777 pass attempts, 58 touchdown passes, and 15 interceptions in 23 games and 23 starts.
Pipkin was signed by the Alouettes on June 5, 2017. Pipkin made his first professional appearance on November 3, 2017, in the last week of the 2017 season. Pipkin completed only two of nine pass attempts for 14 yards. He was released June 19, 2018. He was re-signed by the team on August 6, 2018. Pipkin became the sixth Alouettes quarterback to start a game in the 2018 season when he started in the team's Week 10 match against the Edmonton Eskimos. Pipkin, who was making his first professional start, completed 14 of 25 pass attempts for 217 yards with one touchdown and one interception. Pipkin earned his first career win the following week when the Alouettes defeated the Toronto Argonauts. The Alouettes decided to stick with Pipkin as their starting quarterback despite Johnny Manziel recovering from a concussion. Pipkin struggled in Week 14, throwing four interceptions, two of which were returned for touchdowns, en route to a 32–14 defeat by the BC Lions. In the days following Head CoachMike Sherman announced that Manziel would start in the teams Week 15 match against the Bombers. Pipkin signed a two-year contract extension with the Alouettes on October 28, 2018, and later that day played the second half of the Alouettes' second last game of the season. Pipkin was named the Al's starting quarterback for Week 1 of the 2019 season, ahead of Vernon Adams Jr. Pipkin suffered a lower leg injury in the team's Week 1 loss to the Eskimos, and was expected to miss 4–6 weeks. He returned to action partway through the Al's Week 8 game against the Redblacks, after an injury to Vernon Adams, but Pipkin was unable to lead the team to victory, completing 8 out of 17 passes. Pipkin started in Week 9 for a still injured Adams, but was unable to lead Montreal to a win in the first ever weather shortened game. Vernon Adams returned to the starting role the following week and remained the starter for the remainder of the season while Pipkin was relegated to the third quarterback role. As a backup to Matthew Shiltz who was starting in place of a suspended Adams, Pipkin fumbled the ball on a short yardage plunge at the BC Lions 2 yard line, costing the Alouettes the game. Pipkin was released by the Alouettes on January 30, 2020. His release took effect prior to a series of off-season bonuses due to be paid totaling 23,500 CND over 4 months.
Edmonton
Pipkin was signed by the Edmonton team of the CFL on February 13th, 2020.
