2021 Winnipeg Blue Bombers The 108th Grey Cup Championship Ring

The 108th Grey Cup decided the Canadian Football League (CFL) championship for the 2021 season. Due to the COVID-19 pandemic, the 2020 season was cancelled and the start of the 2021 season was delayed, pushing the game to December 12, 2021. The 108th Grey Cup was a rematch of the 107th Grey Cup in 2019 between the defending Grey Cup and West Division champion Winnipeg Blue Bombers and the East Division champion Hamilton Tiger-Cats, at Tim Hortons Field in Hamilton, Ontario. The Blue Bombers defeated the Tiger-Cats 33-25 in overtime for their second straight title, making them the first team in 11 years to win two straight Grey Cups. This game was also the fourth Grey Cup to go into overtime, with the other three instances coming in 1961, 2005 and 2016.

The Blue Bombers finished a dominant season with the best record in the CFL at 11-3 with two of their losses occurring after already clinching first place in the West Division. The team won their first division title since 2011, and first West Division first-place finish since 1972, after they defeated the BC Lions on October 23. The Blue Bombers then had 42 days until their next meaningful game with a West Final matchup, their third consecutive appearance in the Division Final, against the Saskatchewan Roughriders which was won 21-17. The team was undefeated at IG Field, winning all seven regular season games and one playoff game there.

The Blue Bombers defence in 2021 was among the best in CFL history, with just 13.4 points allowed per game, which was their lowest total allowed since 1958 when they had 11.4 points against per game. The team also allowed just six total points scored in the fourth quarter in the first twelve games of the season. The team's quarterback, Zach Collaros, started 13 games and was named the West Division's Most Outstanding Player after finishing the season with a 111.01 quarterback passer rating, which was the tenth best of all time. The team had 15 Divisional All-Stars, the most in the league, with seven on offence, seven on defence, and one on special teams. Despite perennial All-Star running back Andrew Harris missing half of the regular season due to injury, the Blue Bombers finished second in rushing offence in the league, led behind the team's four Division All-Stars on the offensive line. With their appearance in this year's Grey Cup, the Blue Bombers surpassed Edmonton for the most Grey Cup appearances of all time with 26.