In 2023, the Winnipeg Blue Bombers would take the West Division with an excellent 14-4 record over the second place BC Lions (12-6), while the Toronto Argonauts would take the East Division with an even better record at 16-2 and a comfortable 5-game lead over the second place Montreal Alouettes (11-7). The Calgary Stampeders and the Hamilton Tiger-Cats would also qualify for the post season. In the first round of the playoffs, it was Montreal over Hamilton 27-12, and the BC Lions over Calgary 41-30. In the Division Finals, it was Montreal surprising Toronto with a dominating performance over the top seeded Argonauts 38-17, and the Winnipeg Blue Bombers would take care of the BC Lions 24-13, setting up the match-up for the 110th Grey Cup Championship. The 110th Grey Cup was played on November 19, 2023, at Tim Hortons Field in Hamilton, Ontario, between the West Division champion Winnipeg Blue Bombers and the East Division champion Montreal Alouettes. The Alouettes defeated the Blue Bombers, 28–24. It was the 12th time that Hamilton had hosted the Grey Cup, the previous having been in 2021. Winnipeg opened the scoring with a field goal by Sergio Castillo at 6:28 in the first quarter. After a Montreal two-and-out, Winnipeg then went on an eight-play, 66-yard drive that ended in Brady Oliveira scoring a five-yard touchdown. Montreal then responded with a seven-play, 77-yard drive, highlighted by Austin Mack's 31-yard catch, which ended with William Stanback scoring a 32-yard rushing touchdown to close out the first quarter. The two teams then punted back and forth until Winnipeg's special teams forced a fumble from returner James Letcher Jr. Winnipeg's Dakota Prukop scored on a one-yard quarterback sneak to extend their lead to 17–7. Montreal received the kickoff to begin the second half where Fajardo completed a 33-yard pass to Mack who made a one-handed catch while being pulled down by his left arm by Demerio Houston. On the next play, Fajardo threw a 23-yard touchdown pass to Cole Spieker to cut the Blue Bombers' lead to three points. On the next drive, Winnipeg began on their own 45-yard line and advanced the ball down to Montreal's nine-yard line in seven plays. However, Winnipeg's Zach Collaros was intercepted by Ento in the endzone on a pass that was intended for Kenny Lawler. On the second play of the fourth quarter, Fajardo was intercepted by Evan Holm on a deep pass intended for Mack, which gave Winnipeg possession at their own 21-yard line. However, after Collaros was sacked by Reggie Stubblefield, the Blue Bombers were forced to punt after a two-and-out, where returner Tyson Philpot returned the ball 30 yards to the Winnipeg 28-yard line. The Alouettes had a quick three-play drive that ended in a Mack 13-yard touchdown reception from Fajardo and Montreal took their first lead of the game. On the following kickoff, Janarion Grant returned the ball to Winnipeg's 54-yard line to set up good field position for their next drive. The Blue Bombers then marched down the field in nine plays where Prukop scored his second touchdown on a four-yard run where the team reclaimed their lead and made the score 24–21 with 5:28 remaining. The Alouettes advanced to the 55-yard line, but Fajardo took an eight-yard loss on first down as he was sacked by Shayne Gauthier. Fajardo then rushed for 13 yards to set up a third-and-five where Maas called for a deep pass to Spieker, who made a 31-yard catch at the Winnipeg 19-yard line. On the next play, Fajardo threw a 19-yard pass to Philpot for a touchdown to put the Alouettes ahead 28–24 with 13 seconds left. Fajardo was named the Grey Cup Most Valuable Player and Philpot received the Dick Suderman Trophy for being the Most Valuable Canadian Player of the game.