Due to the Covid-19 pandemic, the 2020 CFL Season was cancelled, with the CFL resuming in 2021. The top three teams form the Eastern and Western Divisons would qualify for the playoffs. Both divsions were pretty balanced, with the exception of the Winnipeg Blue Bombers, who would lead the way with an excellant 11-3 record. The Saskatchewan Roughriders and the Calgary Stampeders would also qualify for the post season from the Western Division. In the Eastern Division, the Toronto Argonauts would take the top spot with a 9-5 record, with the Hamilton Tiger-Cats and the Montreal Alouettes taking the remaining two playoff spots. In the first round of the playoffs, it was the Hamilton Tiger-Cats over the Montreal Alouettes 23-12, and the Saskatchewan Roughriders would get by the Calgary Stampeders 33-30 in overtime. In the Division Finals, it was the Hamilton Tiger-Cats over the Toronto Argonauts 27-19, and the Winnipeg Blue Bombers over the Saskatchewan Roughriders 21-17, setting up the match-ups for the 108th Grey Cup Championship. This was the 11th time that the city of Hamilton hosted the Grey Cup, with the previous coming in 1996, and the first to be played at the new Tim Hortons Field. 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 game was played in windy conditions, with gusts of nearly 50 km/h. Winnipeg won the coin toss, but elected to defer, choosing to play with the wind at their backs in the first and the fourth quarters. Winnipeg used the wind to their advantage in the first quarter, with two field goals and a single, while Hamilton was limited to seven net offensive yards, the lowest scoring opening quarter of a Grey Cup since 2008. Hamilton replied in the second quarter with a field goal and a twelve-yard touchdown just before halftime, giving them a 10–7 lead. In the third quarter, Winnipeg managed to kick a 15-yard field goal into the wind to tie the game. Hamilton then went for it on third down and was stopped, forcing a turnover on downs, but their aggression was rewarded with a 43-yard interception by Hamilton defensive back Kameron Kelly. Hamilton quarterback Jeremiah Masoli threw an 11-yard touchdown on that same drive to make the score 17–10. Winnipeg conceded a safety near the end of the quarter to fall behind 19–10, and early in the fourth quarter Hamilton kicked a 10-yard field goal to go up 22–10. As Winnipeg receiver Rasheed Bailey stated after the game, "The wind was tough. It was tough, in the third quarter, we couldn't get anything going because of the wind." When Winnipeg got the wind back in the fourth quarter, the game began to turn around. Winnipeg kicker Sergio Castillo kicked a 20-yard field goal, and then Winnipeg quarterback Zach Collaros threw a 29-yard touchdown, followed by a kickoff single by Castillo to close the gap to 22–21. With 1:52 left in the game, Castillo kicked his fifth field goal of the game, from 45 yards away, to give Winnipeg a 24–22 lead. He kicked a single on the following kickoff to make it a 25–22 lead. Hamilton responded by driving all the way down the field, nearly scoring a touchdown before settling for a 13-yard field goal with four seconds left in the game. In overtime, Winnipeg drove down the field and Collaros threw a 13-yard touchdown, and made the two-point conversion to make it 33–25. Then, on Hamilton's ensuing position, Winnipeg linebacker Kyrie Wilson intercepted a deflected pass from Masoli, ending the game. Winnipeg quarterback Zach Collaros was named the most valuable player, while Winnipeg receiver Nic Demski was named the top Canadian. Winnipeg became the first team to win back-to-back Grey Cups since the Montreal Alouettes in 2009–2010 (and the first West Division team to do so since the Edmonton Eskimos won five straight from 1978 to 1982), and Winnipeg won back-to-back Grey Cups for the first time since 1961–62. Hamilton extended the longest active Grey Cup drought in the CFL to 22 years.