[5] The match was played on November 24, 2019, between the Winnipeg Blue Bombers and the Hamilton Tiger-Cats at McMahon Stadium in Calgary, Alberta.

[9] Reasons in favour of this were the weather being warmer in October as well as a potential television deal with the American-based NFL Network.

Leading up to the formal announcement, the Hamilton Tiger-Cats and the Calgary Stampeders were the only clubs that publicly expressed interest in hosting the game.

[14] Tiger-Cats CEO, Scott Mitchell, had said that the team wanted to host this game in particular since it coincides with the 150th anniversary of the original Hamilton Football Club.

[6] The Grey Cup Festival ran from November 20 to 23 and was centred around downtown Calgary and the facilities in Stampede Park.

[20] In week 20 of the season, Bombers running back Andrew Harris broke the record for most career rushing yards by a Canadian in the CFL, surpassing Hall of Famer Norm Kwong.

[21] The Bombers were led into the playoffs by quarterback Zach Collaros, who played his first game for the team in the second last week of the season following injuries to Matt Nichols and Chris Streveler.

[23] The following Sunday, November 17, the Bombers played the Western Final against the local rivals Saskatchewan Roughriders at Mosaic Stadium in Regina.

[25] The Tiger-Cats finished the regular season undefeated at home, for the first time in their history, with a record of 9–0 at Tim Hortons Field.

[25] For most of the year, the team was led by rookie quarterback Dane Evans after starter Jeremiah Masoli suffered a season-ending leg injury in the seventh game of the season.

As the first place team in the East Division, the Tiger-Cats received a bye in the first round of the playoffs and hosted the Eastern Final on November 17 against the crossover Edmonton Eskimos.

The first game took place in Hamilton in week 7, where the Tiger-Cats won 23–15 despite losing starting quarterback Jeremiah Masoli to injury in the first quarter.

[28] The two teams did not meet again until week 16 in Winnipeg, where the Tiger-Cats won 33–13, breaking a six-game unbeaten streak for the Bombers at IG Field.

The Bombers immediately answered with a high 30-yard toss from Zach Collaros to Kenny Lawler, but the drive ended with an unsuccessful 48-yard field goal attempt which scored one point.

Hamilton's Lirim Hajrullahu had a 46-yard punt returned 32 yards by Janarion Grant, leaving the Bombers with good field position.

[34] The Blue Bombers began the second half by running down almost four minutes of game time, followed by a 39-yard field goal to make it 24–6.

The Tiger-Cats attempted to respond, but on reaching the opposing 25-yard line were again halted by the Winnipeg defence, who forced another turnover on downs.

Winnipeg took six minutes off the clock with an 80-yard drive down the field which appeared to score a touchdown, but was overturned after television review.

[38] Rock band The Beaches performed during the SiriusXM Kickoff Show while Young Canadians singer Lindsey Kelly, accompanied by the Calgary Stampede Showband sang "O Canada".