The 20 Most Important Moments in Toronto Sports History

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It’s safe to assume that most of you reading this list have no idea who Damon Allen is. But in the world of Canadian League Football, his name evokes a response similar to that of Peyton Manning or Brett Favre in the NFL. A native of San Diego, Allen was a standout at Cal State Fullerton in the early 1980s, but undersized and overlooked, he eventually signed with the Edmonton Eskimos in 1985. He would go on to appear in an incredible 370 CFL games during a career that spanned 23 seasons. In 2006, while playing for the Toronto Argonauts, a then-43-year-old Allen broke the career pro-football yards mark of 70,553 set by former CFL-turned-NFL great Warren Moon, who had retired in 2000. Allen would go on to play one more season and bring his yardage total up to 72,381, a mark that was bested by now-retired Montreal Alouettes legend Anthony Calvillo four years later. 

In 2007, Toronto became the first Canadian city to have a Major League Soccer team. But for the first eight seasons of the club’s existence, it failed to earn a single playoff berth. In 2015, Toronto FC finally broke into the postseason, finishing the year without a losing record for the first time in its history. Unfortunately, the team lost 3-0 to another Canadian expansion franchise, the Montreal Impact, in their only playoff game. But with last year’s MLS Golden Boot, Newcomer of the Year, and MVP award winner Sebastian Giovinco returning for his second season with the squad in 2016, there’s hope that they may soon notch their first postseason victory. 

Fast forward 13 years after the Raptors’ first and only playoff series victory in 2000, and the team found itself an unlikely No. 3 seed in the East. Toronto had just finished with its best regular season record ever (48-34), despite a cast that lacked any true superstar players, and fans in Toronto were pumped about the team in a way they hadn’t been in over a decade. On the morning of the team’s first game in their opening-round playoff series against the Brooklyn Nets, Masai Ujiri, the teams’s newly hired General Manager, decided to speak before a crowd of thousands who’d gathered outside Air Canada Centre. At the tail end of his rallying oratory, the Nigerian-raised executive paused, raised his hand to the sky and shouted, “F*** Brooklyn!” The crowd went wild, and it became clear in that moment that pro basketball in Toronto had reached new heights. 

After the Raptors’ inception in 1995, there was quite a bit of buzz surrounding Toronto’s newly minted NBA franchise. But after stumbling to a 90-206 record, with no playoff appearances during their first four seasons of existence, some of that luster inevitably wore off. In 2000, the team was able to recapture the city’s attention with the emergence of second-year swingman Vince Carter and a 45-37 finish that earned them their first postseason berth. Unfortunately, they were swept 3-0 by the New York Knicks, but one year later they would get their revenge against the Knicks, beating them 3-2 in the opening round of the 2001 Playoffs.

With 16 Grey Cup Trophies (the CFL equivalent to the Lombardi Trophy) on their mantle, the Toronto Argonauts are the winningest franchise in the history of Canadian Football. But for a long time, there was a championship drought in Toronto. After the team won its 10th Grey Cup in 1952, it took them 31 years to grab another, finally doing so in 1983 with eventual Hall of Fame quarterback Condredge Holloway at their helm. It was the city’s first championship of any kind in a major sport since the Maple Leafs won the Stanley Cup in 1967.

In the history of Major League baseball, just 27 players have hit 50 or more home runs in a single season. And perhaps none of them did so more unexpectedly than Blue Jays slugger José Bautista. A career .238 hitter with just 59 home runs to his name in 2,038 plate appearances from 2004-09, he miraculously transformed in 2010 from near replacement-level to home-run king. Bautista knocked an amazing 54 balls into the stands in 683 appearances at the plate that season, finishing fourth in league MVP voting. His home run total that year set a new franchise record and marked the greatest increase from one year to the next in MLB history, 41.

Established as an expansion team in 1977, the Blue Jays got off to a rocky start as a franchise. In each of their first five seasons of existence, the club finished dead last in the American League East, winning just 35.9 percent of their games during that stretch. But over the next three years, the team slowly improved thanks to a young core that featured All-Star pitchers Dave Stieb and Jimmy Key. In 1985, the team finally ended an eight-year stretch without a playoff berth, winning the AL East with a record of 99-62 and making it all the way to the ALCS before losing to the Kansas City Royals in seven games. 

At the height of “Vinsanity,” there was perhaps only one player in the Eastern Conference more idolized than Vince Carter…Allen Iverson. And in 2001, NBA fans were lucky enough to see these two rising superstars go head-to-head in the second round of the playoffs. In Game 3, with the series knotted at one win apiece, Carter went off for 50 points in a 102-78 shellacking of the Sixers at Air Canada Centre, doing so while knocking down nine 3s on 13 attempts. And although Carter and the Raptors eventually fell to top-seeded Philadelphia in seven games, that game is one that many Raptors fans remember as perhaps the most enjoyable in the history of the team. 

In their first season of existence, the Raptors were not a good team. In fact, they were downright dreadful, winning just 21 games en route to the third-worst record in the league. But one of those wins came against perhaps the best NBA team ever assembled, the 1995–96 Chicago Bulls. Early on, the Raptors played their home games at the SkyDome, the 54,000-seat stadium in which the Blue Jays also play. On most nights during their inaugural season about 23,000 fans showed up, an impressive number given the team’s poor performance, but in this late-March meeting, over 36,000 fans packed the stadium to see Michael Jordan and the then 60-7 Bulls take on the Raptors. MJ dropped 36 points on Toronto that night, but Damon Stoudamire scored 30 of his own, to go along with 11 assists, and led the Raptors to a stunning 109-108 victory over the Bulls. 

Many all-time greats have laced up their skates to represent the Toronto Maple Leafs, but in recent history one name stands out above all, Mats Sundin. The Hall of Fame center spent 14 seasons in Toronto, and while the Leafs unfortunately failed to win a Stanley Cup during his tenure with the team, he left as the club’s all-time leader in goals scored, with 420. He officially passed all-time Leafs great Darryl Sittler on Oct. 4, 2007, in a game against the Ottawa Senators.

The Canada Cup was an international hockey exhibition, held five times between 1976 and 1991, that allowed amateur and professional players alike to represent their countries in a worldwide tournament. The 1987 iteration of the event, held in Hamilton, Canada (about an hour southwest of Toronto), was especially memorable because it saw Canada and the Soviet Union square off in the Finals, and the series ended in thrilling fashion. In the final minutes of the final game of the best-of-three series, a masterful goal scored by Mario Lemieux and assisted by Wayne Gretzky lifted Canada to a 6-5 victory. 

Renamed Rogers Centre in 2005, the SkyDome was one of the most advanced facilities of its kind when it opened in 1989. The first stadium ever built with a retractable roof, it allowed the Blue Jays and Argonauts to move on from their former home, Exhibition Stadium, a crude attempt at a multi-purpose complex, completed in 1948 and demolished in 1999. Today, there are now 32 stadiums across the globe with retractable roofs, but it was the SkyDome that paved the way as one of the most unique sports complexes of the late 20th century. 

Holding the No. 4 pick in the 1998 NBA Draft, the Raptors swung a deal on draft night with the Golden State Warriors, picking fifth, in which the two teams swapped picks. Antawn Jamison was sent to California and Vince Carter was sent north of the border, along with cash considerations from the Warriors. The choice to go with Carter over Jamison proved to be one of the best decisions in franchise history. And although the Raptors never made it past the second round of the playoffs during Carter’s six years with the team, the 6-foot-6 slasher’s high-flying style and superstar status helped put Canadian basketball on the map.

Although Toronto-native Anthony Bennett has been one of the most disappointing first-overall selections in the history of the NBA Draft, the mere fact that a Canadian earned that honor (not to mention that Andrew Wiggins did the same, one year later) is a testament to just how far basketball has come for Canada in recent years. From the inception of the NBA in 1949 through 2011, only 19 players with Canadian citizenship had ever played in an NBA game. But in the past five years, 12 more Canucks have joined the list, including Bennett.

Through 1991, the Blue Jays had made the postseason just three times in their 15-year history. In each of those trips to the playoffs, the team was able to reach the American League Championship Series, but they had fallen short of reaching the World Series in all three postseason trips. In 1992, the Jays went 96-66, which still today ranks as the best season in their history. Reaching the ALCS for the second straight season, they finally secured a pennant, beating the Oakland A’s in six games before defeating the Atlanta Braves in six games to notch their first World Series title. 

In 1993, the NBA decided to award expansion franchises to both Vancouver, Canada, and Toronto. It would be two more years before the league’s two newest teams, the Grizzlies (later relocated to Memphis) and the Raptors, would make their on-court debuts, marking the first time a pro basketball team had been based north of the border since the existence of the Toronto Huskies of the Basketball Association of America (which later became the NBA) from 1946–47. 

Julius Erving may be the father of the dunk contest, but Vince Carter is undoubtedly its golden child. After a two-year layoff from the NBA’s dunk contest, the league decided to bring the event back in 2000 for All-Star Weekend in Oakland, Calif. The contestants were Ricky Davis, Steve Francis, Larry Hughes, Tracy McGrady, Jerry Stackhouse, and, of course, Vince Carter. What ensued was one of the most outstanding athletic displays ever seen. Carter rattled off a handful of never-before-seen dunks that put many of the event’s former winners to shame, including two reverse-360 windmills, a honey dip jam, and a between-the-legs slam off an alley-oop bounce pass from McGrady. That was the night Vince Carter went from NBA star to international superstar.

Anyone who’s spent time in Toronto knows that the Maple Leafs are like a religion in that city. Established in 1917, the Leafs won an NHL championship in their very first season of existence. Over the next 49 seasons, they went on to win 12 more championships, but the Stanley Cup Trophy they hoisted in May 1967 remains their last. Nearly 50 years have passed since then, and to many older Torontonians, that 1967 team is remembered with more fondness than perhaps any other the franchise has ever assembled.

While this memory may be a humiliating one for Raptors fans, there is no doubt that the night Kobe Bryant scored 81 points is one of the most memorable sports moments ever to involve the city of Toronto. It happened on Jan. 22, 2006, nearly 44 years after Wilt Chamberlain scored 100 points in a game between the Philadelphia Warriors and New York Knicks, and arguably it was even more impressive given the level of competition Bryant faced in 2006, versus what Chamberlain faced in 1962. Kobe made 28 of the 46 shots he attempted, knocking down 7 of his 13 3-point attempts, and going 18-for-20 from the free-throw line. Amazingly, only 25 of Kobe’s points were assisted, meaning he created 56 points for himself against a helpless Jalen Rose and the Toronto Raptors that night.

In the history of Major League Baseball, only six franchises can boast World Series victories in back-to-back seasons. Thanks to late-game heroics by Joe Carter, and an epic collapse by Phillies closer Mitch “Wild Thing” Williams, the Blue Jays can count themselves among that exclusive company. Going into the ninth inning of Game 6, leading the series 3-1, Toronto trailed Philadelphia 6-5. A walk, a flyout, and a single to center field gave the Jays base runners on second and third, with just one out and Carter at the plate.

He took two called strikes and held off on two pitches outside the strike zone to bring up a 2-2 count, but on the fifth pitch Williams threw a fastball low and inside. Carter smacked the ball cleanly down the left field line, fair and over the wall, for a walk-off home run to end the series and give the Jays their second consecutive World Series title. Already perhaps the most endearing moment in Toronto sports history, its memory was evoked on an international stage last summer when Drake used the iconic image of Joe Carter in the moments after hitting the home run as album art for his “Back To Back” single, a diss track aimed at Meek Mill.