Remember These Iconic Moments in Toronto Sports?
- Toronto
Naomi Brown | May 4, 2026
Naomi Brown is a Vancouver-based writer and reporter
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These Toronto athletes and teams defied the odds and proved the fighting spirit of their city on the global stage. Here are the stories of four of those iconic moments in sports.
1. Olympic Footrace-1997
Two Olympic Gold Medalists, Canadian Donovan Bailey and American Michael Johnson, feuded in the late 90s over who was the official fastest man in the world. Bailey had won the 100m sprint, and Johnson took home gold for the 200m. When Canadian and American media outlets caught wind of the conflict, each pronounced their country’s athlete the faster man.
As the buzz grew, an event to test the athlete’s claims was conceived. A 150 meter race was held in the Toronto SkyDome (now Rogers Arena), drawing 30,000 live spectators and 2.584 million Canadians watching on live television. The race began with Jonson trailing behind Bailey. Halfway through, Johnson injured his quadricep, leading him to lose. Despite the injury, officials concluded the title of World’s Fastest Man indeed belonged to Donovan Bailey, who walked away from the race with a million dollar prize.

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2. José Bautista Bat Flip- 2015
Toronto Blue Jays fans were ecstatic in 2015 when, for the first time since 1993, their team made the MLB postseason. The East Division Champs were fighting for a spot in the American League Championship Series against the West Division Champion Texas Rangers. The best-of-five series started with two Rangers wins in Toronto, followed by two Blue Jays wins in Arlington. The final game at Rogers Centre was all or nothing.
In the bottom of the seventh inning (which lasted 53 minutes), José Bautista stepped up to the plate. The score was tied, and the Jays had runners on first and third. Hitting the ball out of the park for a three-run homer, Bautista flipped his bat in the air– a celebration before his run. While some Rangers players and fans considered the gesture unsportsmanlike or “too showy”, Blue Jays fans remember it as an iconic moment for their team. A viral internet sensation, the bat flip has been printed on shirts, carved into pumpkins and even tattooed!

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3. Kawhi Leonard Buzzer Beater- 2019
In the seventh game of the Eastern Conference semifinals in 2019, the Toronto Raptors won against the Philadelphia 76ers by what would come to be known as “The Shot”. Following a very close four quarters, the score was tied and the Raptors had 4.2 seconds to inbound the ball and score. Who better to pass to than Kawhi Leonard, who— after recovering from an injury for much of his first season with the team– had been shining and carrying them through the post-season.
After catching the ball, Kawhi drove it down court behind the three point line and shot a Hail Mary over his defender from the corner. The buzzer blared and was followed by a second of silence; the ball bounced on the rim four times before dropping in. The stands erupted in disbelief, as the Raptors had just made it to the Eastern Conference Finals.

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4. Toronto FC Wins MLS Cup- 2017
In the 22nd season of MLS history, Toronto FC fought in a final matchup against the rival Seattle Sounders FC. The two teams both made the championship the year before, when Seattle won it in a penalty shootout. Determined to secure the title, the Toronto team played a great 2017 season, winning 20 out of 34 games.
After defeating the New York Red Bulls and Columbus Crew SC, Toronto faced Seattle again at BMO Field. Nearly 2.5 million people tuned into the game between Canadian and US networks. After a scoreless first half, the 67th minute saw a pivotal goal by Jozy Altidore. Another goal during stoppage time was scored by Víctor Vásquez, solidifying the Toronto win. The game was history, as Toronto FC became the first Canadian team to win the MLS Championship.
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