7 Biggest Upsets Suffered in Canadian Sports History

In the 2026 Winter Olympics, Team Canada was a massive -1600 online sports betting favourite against Czechia in the quarterfinal of the men’s ice hockey tournament, where they narrowly avoided an upset loss in overtime. 

However, the nation hasn’t always been so fortunate.

Below are the seven biggest upsets in Canadian sports history.

Biggest Canadian Sports Upsets 

1. Czech Republic vs. Canada: 2-1, 1998 Olympics

In the first Olympics to feature NHL participation, the Canadian team, led by Wayne Gretzky, was expected to waltz its way to gold. 

That was until Czech goaltender Dominik Hasek stymied the Canadian attack and led his nation to a 2-1 victory over the Canadians in the semifinal, with Gretzky controversially being left out of Canada’s shootout lineup.

The Czech Republic went on to win its first Olympic gold medal in men’s hockey, while Canada finished off the podium.

2. Switzerland vs. Canada: 2-0, 2006 Olympics

Switzerland was supposed to be a “warm-up” for a heavily favoured Team Canada, but goaltender Martin Gerber had other ideas. 

Gerber stopped all 49 shots he faced while Canadian-born Paul DiPietro scored both goals to lead Switzerland to its first win over Canada.

3. Matt Serra vs. Georges St-Pierre: Round 1 TKO, UFC 69

In one of the biggest upsets in UFC history, Matt Serra knocked out Georges St-Pierre in the first round at UFC 69 to claim the welterweight title.

St-Pierre was a massive -1300 favourite in the fight, with Serra standing as a +850 underdog.

It marked the second (and final) defeat of GSP’s career, who went on to avenge his loss to Serra a year later, while ending his career with 13 straight wins.

4. Kazakhstan vs. Canada: 6-3, 1998 World Juniors

Canada stumbled through the 1998 World Juniors, posting a 2-2 record in the preliminary round and losing to Russia in the quarterfinal.

However, things got even worse for the Canadians in the seventh-place game when they lost 6-3 to Kazakhstan and finished eighth overall in the tournament – the country’s worst finish at a World Juniors.

5. Latvia vs. Canada: 3-2, 2025 World Juniors

Latvian goaltender Linards Feldbergs stood on his head, stopping 55 of 57 shots and all eight shootout attempts to lead Latvia to its first win against Canada at the World Juniors.

It was the beginning of a disappointing tournament for the Canadians, who later fell to the Czechs in the quarterfinal.

6. Andre De Grasse Misses the Podium: 100m Sprint, 2022 World Athletics Championships

After winning gold in the 200m and bronze in the 100m at the Tokyo 2020 Olympics, Andre De Grasse was considered one of the world’s top sprinters heading into the 2022 World Athletics Championships.

Despite struggling with a foot injury and recent COVID-19 bouts, De Grasse opted to compete. He ran a 10.21 in the semifinals and failed to qualify for the final, marking the first time he did not win an individual medal at Worlds.

7. Tamara Zidansek vs. Bianca Andreescu: First Round, 2021 French Open

Bianca Andreescu became an instant sensation after her magical 2019 run, during which she won the Indian Wells Open, the Canadian Open, and the US Open at just 19 years old.

Andreescu’s performance was hampered by a knee injury and COVID-19 over the next two seasons, with her most stunning loss coming at the 2021 French Open, when No. 85-ranked Tamara Zidansek defeated the No. 6 seed in a match that lasted more than three hours.