Top 10 of the Decade: Biggest Moments for Toronto Sports Fans

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Usually at this time of year, sports media likes to take a look back at the biggest stories of the past 12 months. However, given that we’re quickly approaching 2020, we wanted to take a look back at the 10 biggest accomplishments of the past decade from the perspective of Toronto sports fans. Things got off to a slow start…..but they sure ended on a high note.

  1. Toronto Raptors 2018-2019 Championship

This goes without saying. After a 26 year championship drought in the four major sports, the Raptors won their first ever NBA Title on the back of Kawhi Leonard, Kyle Lowry, and an incredible supporting cast led by emerging superstar Pascal Siakam. The first win by a team based outside the United States, it was an absolutely electrifying 2.5 months capped off by a parade for the ages. 

  1. Bianca Andreescu 

Just a few short months after the Raptors captured the hearts of all Canadians, Bianca Andreescu became the first Canadian to win a Grand Slam singles title at the 2019 US Open. As a teenager! What’s more? She had to defeat the greatest of all time, Serena Williams, to do so. While Serena nears the end of her illustrious career, Bianca’s is just beginning. 

  1. Jose Bautista's Bat Flip

The Bat Flip heard around the world. A true “where-were-you-when” moment. Bautista’s homerun to cap off the 7th inning of game 5 of the 2015 ALDS - one of the wildest innings in playoff history - was the biggest Blue Jays moment since Joe Carter’s walk-off in 1993. A little over four years later, has the bat landed yet?

  1. The Shot

Even if the Toronto Raptors didn’t win the Championship, Kawhi's buzzer-beater in Game 7 vs. Philadelphia in Round 2 of the playoffs would have been remembered as the biggest single shot in Raptors history. With zero seconds left on the clock, the bounces, the crouch, the silence. A truly unbelievable moment. 

  1. Edwin Encarnacion's Walk-Off

If not for Bautista’s bat flip, Edwin’s walk-off in extra innings of the 2016 Wild Card game would have been the Blue Jay’s signature moment of the 2010’s. Needing only a single or sac fly to win it, Edwin demolished an ill-placed fastball to deep left field to win a one game, winner-takes-all matchup between division rivals. 

  1. The Kawhi Leonard - DeMar DeRozan Trade 

In the summer of 2018, the Raptors fearless leader - Masai Ujiri - made the most difficult and risky decision of his career: trade the most beloved and accomplished Raptor in franchise history – DeMar DeRozan - for a top 5 NBA talent, albeit one with injury concerns coming off a season where he played less than 10 games. Despite only playing one season in Toronto, the gamble paid off. Banners fly forever. 

  1. Auston Matthews Four Goal Debut 

Drafted 1st overall, the expectations for Auston Matthews in the centre of the hockey universe were sky high. With the pressure of an entire fan base watching his every move, Matthews did not disappoint in his first career NHL game as he registered four goals in a historic debut. 

  1. TFC 2017 MLS Cup

When Tim Leiweke took over as CEO of MLSE - the owner of the Maple Leafs, Raptors, and TFC - he made it an immediate priority to invest in the MLS club, recognizing the enormous soccer market in the GTA. A few short years later, with a star studded roster including Sebastian Giovinco, Michael Bradley, and Jozy Altidore, the TFC won their first MLS title. 

  1. Penny Oleksiak

At the 2016 Summer Olympics in Brazil, Oleksiak became the youngest gold medalist in Canadian history and the first Canadian to win four medals in the same Summer Games. Oleksiak also set an Olympic record in the women's 100-metre freestyle. Not a bad debut for a 16-year-old!

  1. Argos 2017 Grey Cup 

The Toronto Argos won the 105th Grey Cup led by quarterback Ricky Ray, defeating the Calgary Stampeders 27-24. The 17th championship for the storied franchise was a nail biter, as they erased a 24-16 deficit entering the 4th quarter. 

Honourable Mentions:

  • Andre De Grasse duelling Bolt and winning 3 medals at the 2016 Olympics
  • Millions of fans flood downtown Toronto for the Raptors championship parade
  • Toronto hosted the 2015 Pan Am Games
  • 2016 NBA All Star Game puts Toronto on the map
  • Vladdy’s record breaking HR derby
  • John Tavares comes home

Can the Blue Jays and Maple Leafs follow the Raptors lead and return to glory? Can Andreescu and Oleksiak continue their historic start to their careers? Here’s hoping for more success throughout the 2020’s! 


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Gabriel Diamond
Gabriel Diamond

Gabriel is one of the Co-Founders of True North Sports Camps. He coached AA and AAA baseball at North Toronto Baseball Association from 2006-2013. Currently, Gabriel works full-time in real estate investments and has a passion for sports writing.

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