2008 was another competitive season for the Canadian Football League. Especially in the Western Division, as all four teams won at least ten games, and all four teams qualified for the playoffs. Montreal and Winnipeg would qualify for the post-season in the Eastern Division. In the first round of the playoffs, it was the Edmonton Eskimos upsetting the Winnipeg Blue Bombers 29-21, while the BC Lions would do the same to the Saskatchewan Roughriders 33-12. In the Division Finals, it was Montreal over Edmonton 36-26, while the top-seeded Calgary
Stampeders would take care of the BC Lions 22-18, setting up the match-up for the 96th Greay Cup Championship game. The 96th Grey Cup was held in Montreal, Quebec at Olympic Stadium on November 23, 2008. The Stampeders would win the game 22-14, in front of a crowd of 66,308. The game got off to a slow start with a Damon Duval 14 yard chip shot field goal for Montreal representing all the scoring in the first quarter. The drive was highlighted by a 55-yard completion from Alouettes' quarterback Anthony Calvillo to Jamel Richardson. Sandro DeAngelis answered back in the second quarter with a 44-yard field goal to put the Calgary Stampeders back on even terms at 3-3. However, the Montreal Alouettes responded when Montreal linebacker, Reggie Hunt intercepted a Henry Burris pass, giving the Alouettes the ball near midfield. The Alouettes offense drove the ball deep into Calgary territory before running back, Avon Cobourne scored the game's first touchdown in the second quarter on a 16-yard run. Then, special teams standout Larry Taylor gave the Alouettes great field position again with a 42-yard punt return. Duval again stepped in and made good on his 19-yard attempt to extend the Montreal lead to 13-3. With momentum on the home team's side, the Calgary Stampeders responded late in the first half when Henry Burris threw a 20-yard touchdown pass to wide receiver Brett Ralph, cutting the Montreal lead to 13-10 heading into halftime and taking momentum away from Montreal. In the second half of the game, it was all Calgary Stampeders. In the third quarter, Sandro DeAngelis kicked his second field goal of the game to tie the game 13-13. Montreal took a 14-13 lead after Damon Duval added a punt single, but that was all the offense that Montreal was able to muster in the second half of the game. On Calgary's next possession, Henry Burris put together a 75-yard drive, including runs of 14 and 29 yards for first downs, which led to a short field goal kick from DeAngelis to give Calgary a 16-14 lead. Montreal's offense started to threaten, but the Calgary defense responded. On the first play of the fourth quarter, Anthony Calvillo was intercecpted by Calgary's Dwight Anderson that led to another field goal by DeAngelis to give the Stampeders a 19-14 advantage. Then midway through the 4th quarter, the Alouettes threatened to regain the lead before an errant Calvillo pass was intercepted by Shannon James, which quieted the Olympic Stadium crowd. Sandro DeAngelis then kicked a 50-yard field goal to extend the Calgary lead to eight points and seal their victory, becoming Grey Cup champions for the first time since 2001. Calgary quarterback, Henry Burris threw for 328 yards and one touchdown, leading all rushers with 79 yards and was named the game's Grey Cup's Most Valuable Player, while kicker Sandro DeAngelis kicked five field goals, connecting from 44, 12, 21, 30 and 50 yards out and took home the Grey Cup's Most Valuable Canadian honours.