He played college football at Central Connecticut, and signed with the Cincinnati Bengals as an undrafted free agent in 2019.

He has also been a member of the New England Patriots, Green Bay Packers, Miami Dolphins, Saskatchewan Roughriders, and BC Lions.

[4] Dolegala was a four-year starter for the Central Connecticut Blue Devils, where he threw for 8,129 yards and 48 touchdowns.

After the Bengals drafted Joe Burrow first overall, Dolegala competed for the team's backup quarterback position with Ryan Finley.

[22] The deal ended up not coming to fruition after the Browns signed Kyle Lauletta off of the Jacksonville Jaguars' practice squad.

[25] In his debut performance Dolegala completed 13 of 28 pass attempts for 131 yards with one touchdown and one interception as the Riders were defeated 31–21.

[28] On February 14, 2024, it was announced that Dolegala had signed a one-year contract worth a maximum of $172,800 with the BC Lions.

[30] On September 16, 2024, it was announced that Dolegala had signed a practice roster agreement with the Winnipeg Blue Bombers.