Canadian Sports Rivalries – Toronto Vs. Boston 

It’s June 27th, 2022, and we’re well into the MLB season. The Toronto Blue Jays are hosting their American League East rivals, the Boston Red Sox. Boston and Toronto are almost inseparable in the sports world. Not only do they play each other in three major sports leagues, but they are also in fact in the same division in all of those three leagues, making playoff matchups, conflicts, and flashpoints almost inevitable. The conditions are perfect for a rivalry, so ahead of this three-game series between Toronto and Boston, let’s examine the history between the two cities.

Both cities are northern and cold, making them perfect hotbeds for ice hockey. Boston was the first American side to join the National Hockey League (NHL) in 1924, and on December 3rd that year, they played the two-time Stanley Cup winners the Toronto Maple Leafs (known as the Toronto St Patricks until 1927). Toronto won that first game 5-3 and it wouldn’t be long before the animosity and playoff matchups between these two began.

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They met in the 1933 Stanley Cup Semifinal, and after four hard-fought games that included three overtimes, the game went to a series-deciding fifth game. What followed was the second-longest game in NHL history, and it would take six overtime periods to separate the two sides before the Leafs came out on top 1-0.

Tensions were high when they met the following season. In a December 1933 matchup, Toronto’s Ace Bailey fell hard head first to the ground after a hit from Boston’s Eddie Shore, putting the Leafs forward into a coma. For his actions, Shore was then knocked out by Red Horner in retaliation. After fears that Bailey would not survive the hit, he eventually recovered, but his hockey days were over. He would, however, make up with Shore soon after but this rivalry was now and truly established.

From 1933-1941 the two sides would meet in the playoffs six times, despite the Leafs winning four of six matchups, the Boston Bruins could point to their 1939 4-1 Stanley Cup Final series win over Toronto as the most important series to win between the two in the history of the rivalry.

It wouldn’t be until 1948 that the two sides would meet again in the playoffs, although Boston won the Stanley Cup in 1941, The Leafs were the team of the forties. Ahead of the 1948 matchup, Toronto had won three Cups since 1942, and they proved to be too good for Boston, beating them 4-1 and going on to win the cup again. History repeated itself in 1949 when, once again, they met in the playoffs, and Toronto again won 4-1 and went on to win their eighth Stanley Cup title.

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The 1950s were a quieter decade relatively speaking, with the dominance of Montreal and Detroit at this time, Toronto was left with just one cup win in 1951, but it was one more than Boston. Toronto did also win both playoff matches in 1951, and then a close 4-3 win in 1959.

In 1958, the Leafs appointed Punch Imlach as their new coach and General Manager. One of his first moves was to trade for Boston’s Allan Stanley in exchange for Jim Morrison. Things were a little different in 1958, and Stanley found out he was now a Maple Leaf right before a practice session with Boston in which he would participate in. Stanley used this as an opportunity to rough some Bruins players up as a parting shot.

Punch Imlach, Toronto Maple Leafs

Stanley was one of a few key moves that Imlach made that turned the Leafs into a powerhouse again. The Toronto Maple Leafs achieved dynasty status in the sixties winning four Stanley Cups from 1961-1967, giving them an overall total of thirteen cups, towering above Boston’s three. Toronto was in control of the rivalry, but that didn’t mean that there weren’t signs of things to come in the following decade.

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At this time in the NHL, the Leafs had the advantage of having preference when it came to being able to recruit talent from Ontario. But in 1960, a young defenceman from Parry Sound would slip from their grasp. Despite a recommendation from a Leafs’ scout, Toronto and Imlach chose not to follow up on the player and he would later be signed by the Boston Bruins. The player in question was Bobby Orr.

The Bruins struggled for most of the sixties, but in 1964, they shocked the hockey world by defeating the reigning Stanley Cup-winning Toronto Maple Leafs 11-0. Then in 1966, the Leafs picked up a young Toronto goalkeeper named Gerry Cheevers. Cheevers would go on to become a Hall of Famer just like Orr. Finally, the biggest tipping point came in 1969, ten years after their last playoff series, Toronto and Boston locked horns again.

Bobby Orr in action against the Toronto Maple Leafs

It wasn’t at all close. Boston won game one 10-0, game two 7-0, and then went on to sweep the series 4-0, outscoring Toronto 24-5. Imlach was fired immediately after game four. During the game one blowout, Toronto looked to take out their frustrations. A Pat Quinn hit on Bobby Orr led to a bench-clearing brawl between the two sides and Leafs’ centre Forbes Kennedy set infamous records with eight penalties and thirty-eight penalty minutes in what was Kennedy’s last game for Toronto. It was Boston’s first playoff series win over Toronto since 1941, and just a year later they followed it up with a Stanley Cup triumph in 1970 and again in 1972, flipping the dynamic on its head.

Matchups between Boston and Montreal would dominate the seventies, but Toronto and Boston did have high-stakes playoff matches as well. In 1972, Boston defeated Toronto 4-1 at the quarterfinal stage, and then swept the 1974 quarterfinal series 4-0. The high-profile playoff matches disappeared in the eighties, but there were still some highlights, such as Toronto overcoming a 6-1 defeat to beat the Bruins 7-6 in overtime in 1989. While the rivalry was calming down on the ice, it was only starting to heat up on the diamond.

In 1977, the Toronto Blue Jays became the newest member of Major League Baseball’s (MLB) American League. They were placed in the AL East division where they would join the Boston Red Sox. The Red Sox were one of MLB’s most storied and iconic franchises, playing ball since 1901, and have featured star players such as Babe Ruth, Ted Williams, and Joe Cronin. They had also been American League pennant winners nine times and were World Series champions five times, although they hadn’t been World Series winners since 1918.

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In the rivalry’s infancy, Boston dominated against the expansion Toronto team in the early years, but the mid-eighties would see the two fight it out constantly for AL East supremacy. In 1985, despite losing nine times to Boston, Toronto won their first-ever division title. Boston came roaring back the year after, finishing nine and a half games ahead of the Blue Jays on their way to a World Series appearance. The Detroit Tigers won the AL East in 1987, but the Jays and Sox were neck and neck in 1988. Toronto dominated Boston that year, winning eleven of thirteen matchups, but thanks to their incredible form after the all-star break, which included twenty-four consecutive home wins, the Red Sox finished the regular season 89-73, just ahead of Toronto’s 87-75 record.

In 1989, Toronto famously rallied from a 10-0 deficit to beat Boston 13-11 at the Red Sox’ iconic Fenway Park Stadium on their way to wrestling the division title back. The two continued to trade division titles with the Red Sox winning in 1990, and the Blue Jays winning in 1991. Neither team had gone on to win a championship, but that changed in 1992. For the first time, Toronto made it to back-to-back division titles in 1992, and with players like they Roberto Alomar, Joe Carter, and Juan Guzmán on their side, they reached their first-ever World Series that October.

Against the Atlanta Braves, Toronto captured their first-ever World Series championship after a win in game six. For the first time in MLB history, the Commissioner’s Trophy was going to Canada. Not content with just one championship, the Jays made the World Series again in 1993 and defeated Philadelphia 4-2 to make it back to titles.

Toronto Blue Jays Joe Carter (right) and Pat Borders leap into the air as pitcher Mike Timlin (left) looks on as the Toronto Blue Jays downed the Atlanta Braves to win the 1992 World Series in Atlanta Oct. 24, 1992. The Blue Jays beat the Braves 4-3 to win the series. (CP PHOTO/Hans Deryk)

Meanwhile, it has been three-quarters of a century since the Red Sox last won a World Series championship. After a strike brought the 1994 season to a sudden halt, Boston won the division in 1995, meaning that for nine of the last ten consecutive (full) seasons, either Boston or Toronto had won the division, with the sides combining for three World Series appearances, and two World Series championships (courtesy of Toronto).

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But after 1995, the rivalry died down, with Toronto in particular perpetually failing to make the playoffs even with the addition of Wild Card teams. But for Boston however, the decades of failure had a light at the end of the tunnel. In 2004, the Red Sox finished thirty-one games ahead of Toronto on their way to a first World Series appearance since 1986, and thanks to a 4-0 sweep over the St. Louis Cardinals, Boston secured its first World Series since 1918, breaking one of the longest title droughts in North American sports history.

Boston Red Sox celebrate their 2004 World Series championship (Getty)

While Toronto continued to struggle in the 2000s, finishing above Boston just once from 2000-2009, Boston was now a title-hungry team. David Ortiz, Mike Lowell, and Manny Ramirez starred for Boston as they won another World Series in 2007, tying Toronto for Commissioners Trophies won since the Blue Jays came into existence. Once again, fans from Boston and Toronto had to look elsewhere for their rivalry, and the hardcourt in the mid-2000s provided the newest battleground.

In the National Basketball League (NBA), Toronto and Boston were two of its founding members for the inaugural 1946/47 season. That year, the Boston Celtics won four of their six matchups against the Toronto Huskies, although both teams finished with 22-38 records at the bottom of the NBA East division. But it was one and done for the Huskies, who folded after that first season. Meanwhile, the Celtics went on to become the most successful team in NBA history. By 1995, the Celtics had amassed an unprecedented fifteen NBA championships. In 1995-96, they were once again joined in the NBA by Toronto, now known as the Toronto Raptors.

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While the two teams were both in the Eastern Conference, Boston played in the Atlantic division, whilst Toronto was in the central. Toronto was moved to the Atlantic division in the 2004-05 season, placing Toronto and Boston within the same division just like in the NHL and MLB. Just like baseball in the mid-eighties and nineties, Boston and Toronto were about to go on yet another run of dominance. Toronto won their first-ever NBA division title in 2006/07, but not only did the Celtics win it back in 2007-08, but their big three of Kevin Garnett, Paul Pierce, and Ray Allen also lead them to their sixteenth NBA championship. For the first time since 1986, Boston was NBA champions. From 2007-2018, either Toronto or Boston won the Atlantic Division every year with the exception of the New York Knicks division crown in 2012.

But further championship success eluded them both. Boston had lost to the Los Angeles Lakers in the 2010 NBA championship, and both teams found themselves constantly stifled by the LeBron James lead Cleveland Cavaliers for the last four seasons. In 2018, Toronto traded their franchise player DeMar DeRozan (amongst other assets) for Kawhi Leonard. Leonard had just one year on his contract, signalling the all-in intention from Toronto now that the Cavaliers were no longer the team they had been from 2014-2018. They won the Atlantic Division, and led by Leonard and Kyle Lowry, Toronto made their first-ever NBA Championship finals, and upset the Golden State Warriors in six games, securing Toronto’s (and Canada’s) first-ever NBA championship.

Toronto Raptors guard Kyle Lowry, centre left, holds Larry O’Brien NBA Championship Trophy after defeating the Golden State Warriors. (Frank Gunn/CP)


All this time, Toronto and Boston had never met in the playoffs, but come to the 2020 pandemic bubble playoffs that would all change. Despite the season coming to a halt in March 2020 because of COVID-19, the regular season was shortened and wrapped up in a bubble environment in Bay Lake Florida, where Toronto was awarded the division title after piping Boston to the title by just five wins. Both teams won their first playoff rounds, setting up an Eastern Conference Semi-Final playoff matchup between Toronto and Boston, their first-ever NBA playoff series.

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In a close-run series, the teams needed a game seven to decide a winner, and the Celtics squeezed past the Raptors by just five points, winning the first-ever Raptors-Celtics playoff series. In 2020-21, Philadelphia broke Toronto and Boston’s stranglehold on the Atlantic division. Marking the end of a run that has seen them combine for thirteen of the last fourteen division titles, three Eastern Conference championships, and both sides lifting an NBA Championship. By this point, the rivalry had once again heated up in the MLB and NHL.

Toronto Raptors guard Kyle Lowry (7) drives against the Boston Celtics’ Marcus Smart (36). (Mark J. Terrill/AP)

In 2012, the Boston Red Sox were looking for a new manager. John Farrell, who was currently the manager of the Toronto Blue Jays was their target, and he left his position with Toronto to take up the mantle with Boston. To make matters worse, Farrell went 11-8 against Toronto in the 2013 season, and went on to lead Boston to their third World Series title in nine years.

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Toronto, who had finished last in the AL East that year, did have reasons to be optimistic. By 2015 Toronto had their best team in over twenty years, and signalled their playoff intent in a game against Farrell’s Red Sox on June 12th, 2015. Down 8-1 by the third inning, Toronto stunned the Fenway Park crowd to win the game 13-10. The Blue Jays went on to win their first AL East division title since 1993.

The following season, harkening back to the eighties and nineties, Boston and Toronto were going head to head for the division title. Matchups between the two were close, with the Blue Jays holding a tight 10-9 record over the Red Sox in 2016, but Toronto struggled in September, leaving the door open for Boston to win the division by just four games. However, Toronto would have the last laugh by making it further than Boston in the playoffs.

Boston Red Sox outfielder Alex Verdugo, right, celebrates after hitting a walk-off single during a 6-5 win over the Toronto Blue Jays, Jun 11, 2021. (Elise Amendola/The Associated Press)

While Toronto still couldn’t make it back to the World Series, Boston, who had removed Farrell from his position in 2018 won their ninth World Series title that same year, while the Blue Jays had regressed to no longer being in the playoffs. By the 2021 season, the rivalry was back on, and both teams were involved in a four-way battle in the American League with Seattle and the New York Yankees for just two Wild Card spots. It came down to the very last day, and Boston’s slender 10-9 2021 record over Toronto proved crucial. The Blue Jays needed to win and hope that the Red Sox slipped up to leapfrog them into the playoffs.

Both teams won their games, which combined with the Yankees’ win meant that Toronto was the odd one out by just one win. After decades of cooling, the rivalry between the Blue Jays and Red Sox finally came back to life in the 2010s, just around the same time it also came storming back into the NHL.

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In 2011, the Boston Bruins won their sixth Stanley Cup and were a team that looked set to compete for years. Toronto, meanwhile, had not even made the playoffs since 2004 and had even helped Boston by giving them future Vezina winner and two-time NHL all-star, Tuukka Rask in a 2005 trade. But their paths crossed in the 2013 playoffs, the first playoff meeting between the Bruins and Leafs since 1974.

Toronto overcame a 3-1 series deficit to force a game seven at Boston’s TD Garden, and what followed lives in the memories of both fan bases for very different reasons. Around halfway through the third period, Toronto held a 4-1 lead and looked poised to win the series. Even when the Bruins made it 4-2, the Leafs still had command with less than a minute and a half on the clock. But Boston improbably fired back with goals from Milan Lucic and Patrice Bergeron, stunning the Maple Leafs and forcing overtime. With momentum behind them, Bergeron struck again in overtime to win the game and the series.

An overtime goal off the stick of Patrice Bergeron, left, completed the Bruins’ epic Game 7 comeback against the Maple Leafs. Jared Wickerham/Getty Images

After a thirty-nine-year wait between playoff matchups, they only had to wait five years for their next matchup. The Leafs had a young team with a core of Auston Matthews, Mitch Marner, and Morgan Rielly, and finished just seven points behind the Bruins in the regular season. There was no holding back in this series. In game one Leafs forward Nazem Kadri charged Tommy Wingels, and was given a five-minute major penalty before being ordered to serve a three-game suspension.

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The Bruins once again took a 3-1 lead but once again, the Leafs forced a game seven in Boston. Toronto had a 3-2 lead going into the third period, but Boston blew the Leafs away with four unanswered goals to win the deciding game 7-3, again knocking out the Leafs. Not content with two recent playoff series, they met again in 2019, and this time, expectations in Toronto were high.

The Leafs had added John Tavares to their roster in the 2018 offseason and again finished just seven points behind Boston. Nazem Kadri would again make headlines. In game two, Kadri was injured after a collision with the Bruins’ Jake DeBrusk that went unpenalized. When Kadri came back into the game, he went after DeBrusk by cross-checking him in the head, drawing a major penalty and was again forced to miss games, this time his punishment was to be suspended for the rest of the series.

Toronto won game five to take a 3-2 lead going into a game six match in front of their home crowd at Scotiabank Arena. On paper, this was Toronto’s best chance to beat Boston in the playoffs, but they lost 4-2 to force yet another game seven at TD Garden, and the Bruins won the deciding game 5-1. With their 2019 playoffs series win, Boston had made it six consecutive playoff wins over Toronto, and it marked sixty years since the Leafs had beaten the Bruins in a playoff series. Although the Leafs can always point to having more Stanley Cups, (even if they’re getting a bit dusty).

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Combined, these two cities have nineteen Stanley Cups, seventeen NBA Championships and eleven World Series titles. Boston and Toronto are two of the most successful cities in North American sports and when you include titles in NFL, CFL, and MLS, the trophy count is even more impressive. For just under a hundred years the two cities have been inseparable in sports, often being in each other’s way on the road to success and giving fans of both teams many memorable moments.

This rivalry is always at its best when Boston and Toronto are competitive in at least one sports front, so to have them be as competitive as they are in NHL, MLB, and NBA all at the same time culminates in this being a special era in this Canadian Sports Rivalry, one that hopefully doesn’t end soon.


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