The 1999 Canadian Football League season is considered to be the 46th season in modern-day Canadian football, although it is officially the 42nd Canadian Football League season.

The CFL enters the final season of the 1900s with increased growth in attendance and television ratings after the '98 season.

The '98 season attendance figures showed a 6.1% increase, which surpassed '97 season figures. TSN television ratings grew by 26.6% in the ages 2+ demographic.

The 1998 Grey Cup game viewership increased to 20.5% as 3.06 million viewers watched the Calgary Stampeders defeat the Hamilton Tiger-Cats, 26–24, which surpassed the '97 Grey Cup game.

The 1999 CFL season, along with the 2001 CFL season, would be one of the closest times where an East Division team could have cross over to the West Division for that division's last playoff spot since the introduction of the Cross over in 1995. The Winnipeg Blue Bombers had to only win one more game to go 7–11, to beat the Edmonton Eskimos final standings, both teams finishing with a tie of 6–12 instead, and under the current rule, even if the team in 4th place in the other division has a better season series record (most wins in the match ups between the teams, or most points scored in total in those games), in which case both were tied again and Edmonton still wins the tie with a 75–53 in two games, for a team to cross over it must have a better final standing win record than the 3rd placed team in the other division, so there was no cross over.

Note: GP = Games Played, W = Wins, L = Losses, T = Ties, PF = Points For, PA = Points Against, Pts = Points

The Hamilton Tiger-Cats are the 1999 Grey Cup Champions, avenging last season's championship loss to the Calgary Stampeders with a 32–21 victory, at Vancouver's BC Place Stadium. The Tiger-Cats have won their first championship since the 1986 CFL season. The Tiger-Cats' Danny McManus (QB) was named the Grey Cup's Most Valuable Player and Mike Morreale (SB) was the Grey Cup's Most Valuable Canadian.

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