The 20 Best Canadian Sports Moments of All Time

Attempting to distill 150-plus years of Canadian sports highlights into a single definitive ranked list wasn't easy.

best canadian sports moments
Complex Original

Illustration via Corbin Portillo

best canadian sports moments

Canada's been on a wave in the sporting world the last couple years, so we thought, what better way to celebrate than by power ranking the nation’s very best athletic moments? Of course, attempting to distill an entire 150-plus years of sports highlights into a single definitive list of GOATs isn’t easy (not to mention, it’s basically an open invitation for strangers to shout at you over the Internet). And there’s so much more to the country’s rich sports history than hockey fights. From the early '90s dominance of the Blue Jays to VC’s elbow dunk, Canada’s got MVPs, multi-sport stars, and a combined 501 Olympic medals. Plus, history-making figures in every sport, from tennis to Formula One.

What we're trying to say is, creating this list was stupidly difficult. And that's a good thing. It means the Great White North has got a massive surplus of unforgettable, hair-raising, nation-defining memories on the North American and international sports stages. Be proud, Canada! (And please don't heckle us too hard.) In honour of Canada Day, here's our list of the 20 greatest sports moments in Canadian history.

20. George Chuvalo Pushes Muhammad Ali to a Full 15 Rounds

View this video on YouTube

Year: 1966

To say no one was expecting much from Chuvalo vs. Ali is a serious understatement. The Canadian heavyweight was a late addition to the card, which moved to Toronto’s Maple Leaf Gardens amid backlash to Ali’s anti-Vietnam War stance. That meant Chuvalo got all of 17 days to prepare for the March 1966 fight. But that night, he became the first man to take Muhammed Ali a full 15 rounds. Ali may have won the fight in a unanimous decision, but going toe-to-toe with the GOAT turned Chuvalo into a national hero. (Adding to the legend? While Ali spent the night in the hospital, Chuvalo was out dancing with his wife.) —Rick Mele

19. The Bat Flip

View this video on YouTube

Year: 2015

It’s not just the home run, an absolute moonshot go-ahead blast in a win-or-go-home Game 5. It’s the exclamation point Bautista put on it. Lost in all the post-game wet blanket (and, frankly, kind of racist) hand-wringing about “playing the game the right way” was the catharsis that Bautista’s bat flip represented for the Jays, and Jays fans. After a truly wild 7th inning that saw a total horseshit “controversial” call gift Texas the lead, it was the ultimate clapback. With one flip of the bat, Jose made it clear nothing was going to deny the franchise, or their fans, Toronto’s first playoff series win in 22 years. —Rick Mele

18. Jackie Robinson Breaks the Colour Barrier With the Montreal Royals

View this video on YouTube

Year: 1946

It’s a bit of MLB history not everyone knows: before Jackie Robinson forever changed the game by debuting with the Brooklyn Dodgers—officially breaking the sport’s colour barrier —#42 spent a season with the Dodgers’ AAA affiliate, the Montreal Royals. The plan was to ease Robinson into the spotlight in a friendlier environment, and Montreal fans fully embraced the future Hall of Famer as he tore up the International League, leading the league in batting average and runs scored while stealing 40 bases en route to a championship. —Rick Mele

17. Christine Sinclair Becomes International Soccer's All-Time Leading Goal Scorer

View this video on YouTube

Year: 2020

Mia Hamm and Abby Wambach had set the standard. After all, the United States has been the standard-bearer for women’s soccer for over two decades. So, who would’ve ever thought a Canadian could not only enter the frame, but topple them?

By notching the 185th goal of her career for Team Canada in January, Christine Sinclair became the all-time leading scorer—male or female—in the history of international soccer. She is the greatest soccer player Canada has ever produced, and her 186 goals in 290 matches is a record that will take some beating. Sinclair is an inspiration to women and soccer players all over the world, and she’s not done yet, still hopeful of bettering the bronze medal she collected at the 2012 Olympics whenever the Tokyo Games are held. —Vivek Jacob

16. Mike Weir Wins the Masters

View this video on YouTube

Year: 2003

For most casual golf fans in Canada in the 2000s, there was Tiger Woods and then… well, everyone else. That is, until 2003, when a lefty from Sarnia shocked the country, and the world, by winning the Masters. Weir entered August an underdog, up against the two-time defending champ Woods, and needed a sudden-death playoff to beat Len Mattiace. But he left Georgia as the first Canadian golfer to win a major, bringing the green jacket to the Great White North for the first time in history. —Rick Mele

15. Steve Nash Wins Back-to-Back NBA MVP Awards

View this video on YouTube

Year: 2006

Nash winning back-to-back MVP honours in '05 and '06 was controversial at the time (still is). But by guiding the Seven Seconds or Less Suns to a league-leading 62 wins and the Western Conference Finals in 2005, Steve Nash became the first Canadian to win the award. And by repeating the following year, the point guard joined an elite list of players who’ve pulled off the feat, one that includes Michael Jordan, Wilt Chamberlain, Bill Russell, LeBron James, and other all-time greats. And now a Canadian. —Rick Mele

14. Jacques Villeneuve Wins 1997 the F1 World Championship

View this video on YouTube

Year: 1997

As the son of legendary Ferrari driver Gilles Villeneuve, Canadian racing fans expected big things from Quebec’s Jacques Villeneuve. And the prodigal son delivered: in 1995, he became the first (and still only) Canadian to win the Indianapolis 500. Then, two years later, the colourful fan favourite did one better, bringing home the country’s first Formula One championship title. And Villeneuve did it in suitably dramatic fashion, fending off an effort by rival Michael Schumacher to take him out in the season’s final race. —Rick Mele

13. Canada Wins the Very First Olympic Gold for Hockey

View this video on YouTube

Year: 1920

No other country has won more Olympic hockey hardware than Canada, with a total of 13 gold medals across the men’s and women’s national teams. But you never forget your first. And at the 1920 Summer Games in Antwerp—four years before the inaugural Winter Olympics—Team Canada didn’t just win, they straight-up dominated the competition: outscoring their opponents 29-1 on their way to winning the first-ever Olympic hockey gold medal. And foreshadowing decades of international hockey dominance yet to come. —Rick Mele

12. GSP Dominates in Front of Record-Breaking Canadian Crowd at UFC 129

View this video on YouTube

Year: 2011

George St-Pierre is one of the greatest fighters in MMA history, and on April 30, 2011, the Canadian was able to treat fans in Ontario to their first UFC experience. Fighting Jake Shields, GSP secured one of his nine title defences in front of 55,724 fans—the largest-ever UFC card in North America at the time—at the Rogers Centre. While the fight wasn’t necessarily a classic, that memory in front of a Canadian crowd is one of GSP’s most cherished. —Vivek Jacob

11. Gretzky to Lemieux to Clinch the '87 Canada Cup

View this video on YouTube

Year: 1987

The best team Canada has ever assembled: 12 Hall-of-Famers headlined by Wayne Gretzky and Mario Lemieux. It was the arch-rival Soviet Union on the other end of the ice once again, in a best-of-three final. After splitting the first two games, it would be up to Gretzky and Lemieux to deliver collectively in a game of the highest stakes.

Tied at five goals apiece with less than two minutes remaining in the third period, Canada broke away off a face-off with Lemieux laying the puck off early for Gretzky, back to Lemieux, cue the madness. —Vivek Jacob

10. Penny Oleksiak Becomes Canada's Best-Ever Summer Olympian

View this video on YouTube

Year: 2016

Canada has a rep as more of a Winter Olympics country. That’s undeniable. But in Rio 2016, Penny Oleksiak gave the country something to cheer about by becoming the first Canadian to win four medals at a single Summer Olympics, also making her Canada’s youngest Olympic gold medalist ever. Not bad for a 16-year-old kid from Toronto’s first trip to the Olympics. —Rick Mele

9. Kawhi Leonard Makes The Shot

View this video on YouTube

Year: 2019

A lot of things had to break just right in order for the Raptors to win the franchise’s first-ever NBA championship, and out of all of them, Kawhi’s last-second, series-winning dagger still feels like the most improbable. A shot that had no business going in, for a team everyone expected to wilt under the pressure, from a player no one could figure out. It defied logic, physics, and pundit predictions—no other moment sums up the Raptors’ 2019 season better. —Rick Mele

8. Sidney Crosby's Golden Goal

View this video on YouTube

Year: 2010

At 22 years old, Sidney Crosby scored the defining goal of his career. Sure, he has Stanley Cups and an array of individual awards to his name, but no moment will top scoring the golden goal to secure Canada’s gold medal in Vancouver in 2010.

"Just as a kid growing up watching the Olympics, dreaming of playing for Team Canada—to be part of that whole experience and just the way it all worked out was really special," Crosby said. "I mean, we won a gold medal. Regardless of the outcome, it would have been special in its own right—but to finish that way, it's every kid's dream." —Vivek Jacob

7. Vince Carter's Dunk Contest Performance

View this video on YouTube

Year: 2000

The moment the basketball world just seemed to stop. Each dunk was more logic-defying than the previous one. Through the legs, elbow in the rim, effortless 360 windmills, these were things that no one had ever seen before Vince Carter made the stage his own in Oakland. From shout-outs in countless hip-hop songs to Donovan Mitchell paying tribute to it nearly 20 years later, it's a moment that inspired a generation and summed up the hype Carter brought to Canada. Let's go home, ladies and gentlemen. —Vivek Jacob

6. Donovan Bailey Becomes the World's Fastest Man

View this video on YouTube

Year: 1996

Watch the moment now and the hairs on the back of your neck will still rise. No one expected the fastest man on the planet to be Canadian. Even when Ben Johnson did it, it was proven too good to be true within 48 hours.

The backdrop of that shame, the vindication of this moment, Donovan Bailey is forever a Canadian icon. —Vivek Jacob

5. The Terry Fox Marathon of Hope

View this video on YouTube

Year: 1980

Diagnosed with osteogenic sarcoma (bone cancer) at just 18 years of age and having his right leg amputated just above the knee, Fox decided to fight against cancer by raising awareness with the Marathon of Hope.

Eighteen months, 5,373 kilometres. From St. John’s, Newfoundland to Thunder Bay, Ontario, until the cancer had spread to his lungs, Terry Fox made not just the nation of Canada but the world stop and take notice. Over $750 million has been raised to date for a legacy that will live forever. —Vivek Jacob

4. Bianca Andreescu Wins the U.S. Open

View this video on YouTube

Year: 2016

She The North has been the most electrifying tennis movement in Canadian history. Daniel Nestor has served the nation proudly, Eugenie Bouchard had her hot streak, and Milos Raonic made a Wimbledon final, but the incredible run that saw Bianca Andreescu not only claim her local Rogers Cup but the U.S. Open with a win over Serena Williams in front of a raucous New York crowd cemented her place in history forever. —Vivek Jacob

3. Paul Henderson's 1972 Summit Series–Winning Goal

View this video on YouTube

Year: 1972

An eight-game series played across Canada and the Soviet Union in the midst of the Cold War. Professionals didn’t participate in the Olympics back then, and with the Soviets dominating the international scene, this was Canada’s chance to prove they were indeed the gold standard.

Effectively trailing the series 3-1 after five games (one tie), Paul Henderson scored the winning goal in each of the next three games to secure a miraculous comeback for the Canadians, the final goal estimated to have been watched or heard by at least two-thirds of the Canadian population at the time. —Vivek Jacob

2. Joe Carter Makes the Toronto Blue Jays Back-to-Back Champions

View this video on YouTube

Year: 1993

It’s not just that the Jays won back-to-back titles in '93an achievement special enough in its own rightit’s how they did it, with a scene cribbed straight from every baseball fan’s childhood fantasy: Down by one with two on and one out in the bottom of the ninth. And one swing of the bat sends everyone home happy.

Only Carter got to actually live it. And every Jays fan got to live vicariously through him, watching him run, skip, and jump around the bases as he touched 'em all. In that moment, we were all Joe Carter, jumping around our living rooms in joyous disbelief. —Rick Mele

1. The Toronto Raptors Become NBA Champions

View this video on YouTube

Year: 2019

The moment that may yet prove the biggest catalyst of basketball growth in Canada. The country that has forever been synonymous with hockey turned up in record numbers to witness the Toronto Raptors become the first Canadian team in NBA history to take home the Larry O’Brien trophy.

Vince Carter may have triggered the initial spurt in basketball growth but Kawhi Leonard and the We The North era will forever be remembered for associating the Raptors with perennial and ultimate success. Years from now, when Canada is competing with the USA on the international stage for bragging rights, we’ll look back on the Raptors’ championship being the biggest trigger. Vivek Jacob

Latest in Sports