[14] It was confirmed on November 13, 2018, that the Tiger-Cats were indeed making a bid for the game as team representatives made their presentation to the league head office in Toronto the week prior.

The Tiger-Cats' president of business operations, Matt Afinec, confirmed that the club had support from Hamilton's mayor, Fred Eisenberger, and that three bids for the Grey Cup game had been made.

[27] The Blue Bombers secured a playoff spot with eight weeks left in the regular season with a victory over the Saskatchewan Roughriders in the Labour Day Classic on September 4.

[29] The team finished with a 10–1 division record with the lone loss coming from the BC Lions after the Blue Bombers had already clinched first place and were resting starting players.

The Blue Bombers defeated the Lions in the West Final by a score of 28–20 behind a strong rushing performance by Brady Oliveira and a punt return touchdown by Janarion Grant.

[33] The team qualified for the playoffs in week 13 and clinched a first-place finish in the penultimate regular season game against the Montreal Alouettes, who were also contesting first place in the East.

[32] Defensive end Ja'Gared Davis would play in his sixth consecutive Grey Cup game, but sought just his second championship after winning with the 2018 Calgary Stampeders.

[38] Trailing by seven points with 30 seconds left in the game, McLeod Bethel-Thompson threw a two-yard touchdown pass to Markeith Ambles, but placekicker Boris Bede missed the potential game-tying convert and the Blue Bombers held on to win 23–22.

[39] However, the Blue Bombers wore their road white jerseys with gold pants which were the same uniforms worn in the previous two Grey Cup games by the team.

Winnipeg immediately answered with a nearly 40-yard throw to Rookie of the Year Dalton Schoen, beginning a drive that ended in a short touchdown rush by Dakota Prukop.

[40] The second half opened with a poor punt by Marc Liegghio giving Toronto prime field position, allowing them to strike quickly with an A. J. Ouellette touchdown.

[40] For the first play of the fourth quarter, John Haggerty punted the ball down to the Winnipeg eight-yard line, only for it to be returned for a Grey Cup record 102-yard touchdown by Janarion Grant, but Liegghio's kick for the convert went wide.

Toronto was only able to muster a field goal in response to make the score 23–17, and were unable to capitalize on an interception soon after, with Chad Kelly replacing an injured McLeod Bethel-Thompson at QB.

Liegghio then produced another poor punt, the return by Javon Leake taking the ball past the line of scrimmage, putting Toronto in prime position once again.

[40] On Winnipeg's first play after the kickoff, Zach Collaros was picked off by Hénoc Muamba with just over three minutes to go, giving Toronto the ball again at the edge of field goal range.

On 3rd-and-13, Toronto managed to sack Collaros, on the second consecutive play, to potentially end the game, but Robbie Smith picked up a face-masking penalty to extend Winnipeg's hopes.