2016 was truly the year of the Underdog, and was another excellant example for the old expression, "That is why they play the games."The Calgary Stampeders would completely dominate the regular season by finishing with a sparkling 15-2-1 record and finishing first in the Western Division of the Canadian Football League. Three other teams in the Western Division would qualify for the playoffs:  the BC Lions (12-6-0), the Winnipeg Blue Bombers (11-7-0), and the Edmonton Eskimos (10-8-0). In the Eastern Division, the Ottawa Redblacks would win the division despite having a losing record (8-9-1), and the Hamilton Tiger-Cats (7-11-0) would also qualify for the post-season. In addition to qualifying for the playoffs with a losing record, the Redblacks would also receive a first-round bye for winning the division. In the first round of the playoffs, it was the Edmonton Eskimos getting by the Hamilton Tiger-Cats 24-21, while the BC Lions would win a thriller over the Winnipeg Blue Bombers 32-31. In the Divisional Finals, it was the Redblacks over the Eskimos 35-23, while the Stampeders would have no trouble with the Lions 42-15, setting up the match-up for the 104th Grey Cup. The game was played on November 27, 2016 at BMO Field in Toronto, Ontario. In an upset, Ottawa defeated the heavily favoured Stampeders 39–33 in overtime to win a championship in just their third season of existence. This was the third Grey Cup game to go
into overtime (the other two instances came in 1961 and 2005). Coming off a season in which they had appeared in the Grey Cup in just their second season of existence, the Redblacks failed to match their 12–6 record of 2015. Nevertheless, they managed to finish in first place in a weak East Division with an 8–9–1 record, becoming the first CFL team to finish first in their division with a losing record. In another CFL first, the Redblacks faced the defending champion Edmonton Eskimos (who, as a crossover team, had defeated the Hamilton Tiger-Cats in the Eastern Semi-Final) in the first-ever Grey Cup rematch to take place in a division final. Despite being underdogs to the 10–8 Eskimos in the Eastern Final, the Redblacks avenged their 2015 Grey Cup loss with a 35–23 win over Edmonton to advance to their second consecutive championship game. Calgary entered the game as the heavy favourites, but it was Ottawa that opened the scoring in the game with a touchdown by Burris halfway into the first quarter, capping off a 65-yard opening drive. The Stampeders responded two minutes later with a 79-yard drive of their own which ended with a touchdown pass from Bo Levi Mitchell to the regular season's Most Outstanding Canadian Jerome Messam, tying the game up at 7–7. Redblacks kicker Ray Early would kick a field goal before the end of the first to put the Redblacks ahead 10–7. In the second quarter, the Redblacks continued to score, with Burris connecting with running back Patrick Lavoie for another touchdown with 6:46 remaining and Early
scoring another field goal with eight seconds left to put the team up at halftime 20–7. The Redblacks defense intercepted two passes by Mitchell in the second quarter, after Mitchell had thrown only eight in the entire season. The Redblacks opened the third quarter with another touchdown, this time from Burris to receiver Brad Sinopoli, to make the game 27–7. This was the largest lead of the game for the Redblacks, however, as in a repeat of the 103rd Grey Cup, they found themselves fending off a fierce second-half rally by their opponent. Halfway through the third quarter, Stampeders kicker Rene Paredes connected on a field goal, and on the Stamps' next Possession, Mitchell would throw a touchdown pass to wide receiver Lemar Durant to bring the Stampeders within ten points by the start of the fourth quarter. Backup quarterback Andrew Buckley would run for a touchdown a minute into the fourth, making the score 27–23 (Parades missed the subsequent convert kick). The Redblacks would respond eight minutes later with a one-yard touchdown run by Burris (and a missed convert kick by Early) to make the score 33–23 with six minutes to play in the game. With under two minutes left to play in the game, Stampeders wide receiver DaVaris Daniels scored a touchdown to bring the Stampeders within three points. After recovering an onside kick, the Stampeders threatened to end the game with a touchdown and made it to the two-yard line before the Redblacks defense managed to hold them back after a controversial play that saw the Stampeders hand the ball to Buckley – their third string quarterback – instead of Mitchell or Messam, the CFL's MOP and MOC, respectively. On their final play of regulation, the Stampeders settled for a field goal to tie the game 33–33 and force overtime. The Stampeders won the coin toss to decide which team would be on offense first, and chose to play second. On the Redblacks' first drive in overtime, Burris threw an 18-yard touchdown pass to Ernest Jackson to go ahead 39–33. After Ottawa failed on the requisite two-point convert attempt, the Stampeders were unable to respond with a touchdown of their own; quarterback Bo Levi Mitchell threw three consecutive incomplete passes to end the game, sealing victory for the Redblacks. Redblacks quarterback Henry Burris was named the Grey Cup's Most Valuable Player, having completed 35-of-46 passes for 461 yards and three touchdowns (while running for another two). Redblacks receiver Brad Sinopoli received the Dick Suderman Trophy as the game's Most Valuable Canadian. Burris became the oldest quarterback to ever win the Grey Cup at 41 years and 177 days.