2019 was, once again, a very competitive season, especially in the Western Division, as four teams qualified for the playoffs.  Saskatchewan (13-5) led the way, finishing one game ahead of second place Calgary (12-6).  In the East, it was Hamilton (15-3) dominating the division, finishing with a comfortable 5-game lead over second place Montreal (10-8).  In the first round of the playoffs, it was the Edmonton Eskimos over the Montreal Alouettes 37-29, while the Winnipeg Blue Bombers would crush the Calgary Stampeders 35-14.  In the
Division Finals it was the top-seeded Hamilton Tiger-Cats over the Edmonton Eskimos 36-16, while the Winnipeg Blue Bombers would continue their Cinderella story by upsetting the division-winning Saskatchewan Roughriders 20-13, setting up the match-up for the 107th Grey Cup Championship.  The game was played on November 24, 2019 between the Winnipeg Blue Bombers and the Hamilton Tiger-Cats at McMahon Stadium in Calgary, Alberta. Winnipeg defeated Hamilton, 33–12.  This was the Blue Bombers' first Grey Cup victory since 1990 (and first as a West Division team since 1984, after two victories as an Eastern team), ending one of the longest championship droughts in CFL history.  The Winnipeg defense started the game well, forcing two turnovers in the first five minutes of game time.  The second turnover was a Willie Jefferson quarterback sack that caused Dane Evans to fumble, losing 35 yards.  This led to an Andrew Harris rushing touchdown on the
next play, giving the Blue Bombers a 7–0 lead.  Hamilton moved down the field quickly with two long catch-and-runs by Brandon Banks, but a pair of unsuccessful running plays limited them to a field goal, cutting the lead to 7–3.  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.  A promising Tiger-Cats drive was ended by David Watford failing a 3rd-and-1 quarterback sneak.  This ended the first quarter, with
the score 8–3 for Winnipeg. The teams traded field goals in the first part of the second quarter to make the score 11–6.  Hamilton's Lirim Hajrullahu had a 46-yard punt returned 32 yards by Janarion Grant, leaving the Bombers with good field position.  They were able to take advantage, with Harris providing 40 of the drive's 50 yards in two plays, including receiving a touchdown to make the score 18–6.  The halfended with a short Justin Medlock field goal for Winnipeg, extending their lead to 21–6.  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 defense, who forced another turnover on downs. However, Winnipeg went two-and-out.  Hamilton capitalized with an eight-play touchdown drive, but missed the two-point conversion to leave the score 24–12.  With three minutes left in the quarter, the Bombers moved quickly down the field with a Drew Wolitarsky 45-yard catch-and-run play, leading to another field goal and a score of 27–12 Two touchdowns behind, Hamilton had no success in the fourth quarter.  They were forced to punt after a 47-yard pass to Mike Jones (Hamilton receiver) inside the 10 yard line was knocked away by Mike Jones (Winnipeg defensive back).  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.  They settled for a field goal and a 30–12 lead with only 6:12 to go.  The Blue Bombers defense then did its part, sacking Evans on the next two plays for two fumbles and another turnover.  Winnipeg took possession and scored another field goal, giving them a 33–12 lead.  With this goal, Justin Medlock tied the Grey Cup records for field goals made (6) and attempted (7) in a single game.  Winnipeg had scored points on seven of their last eight possessions.  The game ended without further incident, giving Winnipeg a 33–12 victory.  Blue Bombers running back Andrew Harris was named the game's Most Valuable Player and also received the Dick Suderman Trophy as the game's Most Valuable Canadian, the first time a single player had won both awards.