The last major accomplishment for Canada football (men) was winning the 2000 CONCACAF Gold Cup.
The Gold Cup was a recent tournament at the time, making its debut in 1991. United States was the first champion, overcoming Mexico in the semifinals, and Honduras in the final. Mexico dominated the next three Gold Cups, until Canada ended their hegemony in 2000.
In order to compete in the Gold Cup, Canada had to participate in a Qualifying Tournament in 1999, since the country was ranked Nº10 at CONCACAF. Canada and Haiti finished first and second respectively, taking part in the cup.
CONCACAF Gold Cup 2000
Canada was drawn in Group D with Costa Rica and South Korea. Costa Rica finished first, even though all three teams had the same amount of points. The reason was that Costa Rica scored four goals, with Canada and South Korea scoring two apiece. With both countries having the same amount of points and goals scored, a coin toss was used. Fortunately for the Great White North, the coin flip was in their favor, reaching the quarter-finals against Mexico.
Canada upset Mexico, coming from behind to beat the current champions with a Golden Goal in extra time. The goals were from Carlo Corrazin (min. 83) and Richard Hastings (min. 92).
In the semifinals, a solitary goal by Mark Watson (min. 68) was enough for Canada to advance to the final. Craig Forrest was the hero of the match, saving a penalty and various shots from the Trinidadian players.
Colombia, South American guest, awaited in the final. In an empty stadium, Canada showed confidence, beating Colombia two to nil with captain Jason de Vos and Carlo Corrazin getting on the scoresheet. Forrest again shined, saving a crucial penalty.
The team, managed by former German player Holger Osieck, showed everyone what they were capable of. Craig Forrest was selected as the Most Valuable Player and included in the team of the tournament. Jason de Vos and Carlo Corrazin were also included.
After this accomplishment, Canada has not won any other major tournament or even qualify to any World Cup.