2000 was another competitive season for the Canadian Football League, as 7 of the 8 teams won at least 7 games. Leading the way in the West as Calgary (12-5-1) would finish with a 2.5 game lead over Edmonton (10-8-0), while Montreal (12-6-0) would finish with a very comfortable 3 game lead over Hamilton (9-9-0). In the first round of the playoffs, it was Winnipeg upsetting Hamilton 22-20, while the BC Lions would to the same to Edmonton 34-32. In the Division Finals, Montreal would roll over Edmonton 35-24, while the BC Lions would continue their Cinderella story by upsetting the top-seeded Calgary Stampeders 37=23, setting up the match-up for the 88th Grey Cup Championship. The 88th Grey Cup was held in Calgary, between the BC Lions and the MOntreal Allouettes, on November 26, 2000. The BC Lions would win the game 28–26. The Lions, who finished 8–10 with an overtime loss during the regular season, became the first team ever to finish with a regular season record below .500 and win the Grey Cup. The game started off slowly. There was no score until Lui Passaglia's missed field goal produced a single for the Lions that got them off to a 1–0 lead. A little more than three minutes
later, Damon Allen scored a touchdown on a one-yard run that made the score 8–0. Montreal finally got on the scoreboard at 11:38 when Terry Baker hit a nineteen-yard field goal to cut the score to 8–3. There was only one score in the second quarter, as Passaglia missed another field goal that produced another single for the Lions. The Lions led 9–3 going into the half. In the third quarter, the Alouettes cut the score to 12–10 after slotback Jock Climie caught a one-yard pass from Anthony Calvillo. Only 55 seconds into the fourth period, Robert Drummond broke through the Al's defense for a forty-four yard score to increase the Lions' lead to 19–10. Terry Baker had his second field goal of the day to bring the Al's nearer, 19–13. Lions' quarterback Damon Allen ran for his second touchdown of the day. The two-point conversion failed, but the lead was now twelve with 11:01 on the clock. Alouettes running back Mike Pringle, who ran for 115 yards on the day, ran in a five-yard score to shrink the score once again to 25–20 with 3:42 left in the game. Lui Passaglia's 29-yard field goal with 1:25 left gave the Lions an eight-point lead. Anthony Calvillo and the Al's only had a small amount of time to work with to possibly tie up the game and send it into overtime. Calvillo hit receiver Ben Cahoon across the middle and Cahoon raced fifty-nine yards to pull the Alouettes to within two with 44 seconds left in the game. The Alouettes went for a two-point convert to tie the game and send it into overtime, but Calvillo's pass sailed over the head of a falling Thomas Haskins, who fell to the turf before the pass arrived. The play was not without controversy, with the Alouettes seeking a pass interference call, but none was called. Montreal attempted an onside kick, but Lions' receiver Alfred Jackson leapt over several Alouette players to recover the football, enabling the Lions to run out the clock. Drummond, who ran for 122 yards on 10 carries, was awarded the game's most valuable player and Millington received the game's most valuable Canadian.