Jeffcoat won the 107th and 108th Grey Cup when the Blue Bombers defeated the Hamilton Tiger-Cats to conclude the 2019 and 2021 seasons.

Jeffcoat was signed by the Seattle Seahawks as an undrafted free agent in 2014, and also played in the National Football League (NFL) for the Washington Redskins and the Cleveland Browns.

Over his final three seasons, he recorded 259 tackles, 25.5 sacks, 56 TFL, 42 pressures, four PBU, three forced fumbles, two interceptions, two blocked kicks, and a touchdown.

[4] As a senior in 2013, he was a consensus All-American and won the Ted Hendricks Award in recognition of his contributions on the field.

[12] In the Week 16 win against the Philadelphia Eagles that removed them from playoff contention, Jeffcoat recorded his first career sack on quarterback Mark Sanchez.

In Winnipeg's one postseason game, Jeffcoat had 5 tackles and a sack, but the Blue Bombers were defeated by Edmonton.

2018 saw Jeffcoat miss several games with injury, but he still put up a respectable 21 tackles, 5 sacks, and 2 forced fumbles.

In the 2019 Grey Cup, Jeffcoat had 4 tackles, 2 sacks and forced a fumble, which he recovered as the Blue Bombers went on to win 33-12.

Jeffcoat was named a CFL All-Star for the first time in his career, as he helped the Bombers win consecutive Grey Cups.