Masoli has also been a member of the Omaha Nighthawks of the United Football League (UFL), and the Edmonton Eskimos, Hamilton Tiger-Cats, and Ottawa Redblacks of the CFL.

Jeremiah Taeatafa Masoli was born August 24, 1988, in San Francisco, California where he spent some of his life before moving to Hawaii.

[8] Masoli helped the Ducks win the Pac-10 Championship, advancing them to the Rose Bowl where they lost to the Ohio State Buckeyes 26-17.

[14][15] Media outlets reported on July 25, 2010, that Masoli had sent his scholarship release papers to a number of schools, notably Ole Miss.

The report included Ole Miss rival Mississippi State, Hawaii, UNLV, Louisiana Tech, and Syracuse.

In a press release, the NCAA stated that the transfer exception cited in Masoli's case is intended for students pursuing new academic study, not avoiding disciplinary punishments.

Ole Miss coach Houston Nutt expressed his disagreement with the NCAA's ruling; some reports suggested that Masoli was likely to be named a team captain for 2010 given his eligibility.

[21] On September 3, 2010, the ad hoc NCAA Subcommittee for Legislative Relief granted Ole Miss's appeal, allowing Masoli to play immediately in the 2010 home opener versus Jacksonville State University.

[23] On April 9, 2011, at the Ole Miss Spring game, Masoli was honored with the 2010 Leadership Award from the Birmingham Alumni Club.

He played in both preseason games leading into the 2013 CFL season, completing 6 of 13 attempts for 88 yards with no touchdowns or interceptions.

[30] Masoli began the 2015 CFL season as the third quarterback on the depth chart, trailing Zach Collaros and Jeff Mathews.

In the Eastern Semi-Final, Masoli lead the Tiger-Cats over the Toronto Argonauts completing 12 of 18 passes for 141 yards, one touchdown and an interception.

[32] Masoli lead the Tiger-Cats into the CFL's inaugural game at BMO Field and the 2016 season opener completing 27 of 37 pass attempts for 318 yards, with three touchdowns and no interceptions, en route to a 42–20 victory.

The Tiger-Cats struggled mightily in 2017, losing their first eight games of the season resulting in Kent Austin stepping down as head coach to be replaced by June Jones.

[41] Masoli and the Ti-Cats got off to a hot start in 2019, winning four of their first five matches, however, he suffered a torn ACL in the team's Week 7 victory.

[43] He was a pending free agent heading into the 2021 season, but instead chose to sign a contract extension with the Tiger-Cats on January 27, 2021.

Following the season the Tiger-Cats renewed Dave Evans' contract, leaving Masoli to become a free agent on February 8, 2022.

[48] Marino was ejected from the game and a couple days later it was reveled that Masoli would miss the next 10–12 weeks or longer with a bone related injury in his leg, not a ligament tear as was originally suspected.

[51] He ended up missing the first three games of the season, and was announced as the starting quarterback for the club's Week 5 match against the Hamilton Tiger-Cats.

[63] Masoli later entered guilty pleas to both the marijuana and failure to stop charges (both non-criminal violations in Oregon).