Bobby Orr, Boston Bruins, Darryl Sittler, Gerry Cheevers, Toronto Maple Leafs

Bruins’ Rivalries Revisited: Toronto Maple Leafs

When the puck drops on the 2023-24 NHL season, the Boston Bruins will be celebrating their centennial. Joining the league as one of the Original Six, the Bruins have formed rivalries with many teams over the years. Today we’ll revisit the long-standing rivalry with the Toronto Maple Leafs.

Led by Jack Adams, Toronto Wins First Game on Dec. 3, 1924

The two franchises met for the first time on Dec. 3, 1924, nearly 100 years ago, when the Bruins lost to the Toronto St Pats, as they were called back then. Jack Adams, a center for Toronto, scored three goals en route to a 5-3 victory.

Jack Adams (centre) after Detroit’s 1955 Stanley Cup Win

Inducted into the Hockey Hall of Fame in 1959, Adams is the only person to win the Stanley Cup as a player, head coach, and general manager. The Jack Adams Award, handed out to the most outstanding coach in the NHL each season, was named after him in 1974.

First Playoff Series 1933 Semifinals

In 1933, the Bruins met the Maple Leafs for their first-ever playoff meeting. With a chance to play for the Stanley Cup on the line, the best-of-five series came down to a fifth game and made history on the way.

The game was a goaltending duel between legendary Bruins’ netminder Tiny Thompson and the Maple Leafs’ Lorne Chabot. Toronto won the game 1-0 in the sixth overtime period in what became the longest game at that point in the early years of the NHL. It was surpassed just three years later on March 24, 1936, by the Montreal Canadiens and Detroit Red Wings. Today, it still serves as the second-longest game in NHL history and one of only two games to go six overtime periods.

1939 Stanley Cup Final

The Maple Leafs won the next three playoff series, as the two clubs met again in 1935, 1936, and 1938. However, the Bruins put a halt to their playoff losing streak when they faced the Maple Leafs in the 1939 Stanley Cup Final. It stands as the only time both franchises played each other in the Cup Final.

The Bruins’ roster featured future Hall of Famers Bobby Bauer, Frank Brimsek, Dit Clapper, Roy Conacher, Bill Cowley, Woody Dumart, Milt Schmidt, Eddie Shore, and Cooney Weiland. The Maple Leafs also had several future Hall of Famers of their own on their roster including Syl Apps, Turk Broda, Gordie Drillon, Red Horner, and Busher Jackson. The Bruins’ and Maple Leafs’ coaches, Art Ross and Dick Irvin, also were Hall of Fame inductees.

The Bruins won the series in five games, with their goaltender Brimsek limiting the Maple Leafs to just six goals. Conacher led the Bruins in scoring with five goals, including the eventual game-winner to clinch the Cup win on home ice at the old Boston Garden.

Bruins Beat Maple Leafs in the 1941 Semifinals

In 1941, led by the “Kraut’ line featuring Schmidt, Dumart, and Bauer, the Bruins and Maple Leafs met again in the playoffs. This time it was in the semifinals and they battled to a deciding Game 7.

The Kraut Line during WWII

The Bruins won the series, narrowly topping the Leafs by a score of 2-1 in the decisive game. The win set up a meeting with the Detroit Red Wings in the Stanley Cup Final. Schmidt and the Kraut line were too much for the Red Wings to handle, and the Bruins were crowned Stanley Cup Champions for the second time in three seasons.

The Maple Leafs won the next four playoff meetings between the clubs, culminating with a 1959 Semifinal win. The 1959 series is the last time Toronto has come out victorious against the Bruins in a playoff series, making it the current longest playoff drought against one opponent.

Maple Leafs Miss Out On Bobby Orr

Before the NHL Entry Draft existed as we know it now, clubs would scout up-and-coming players and sign them to “A,” “B,” or “C” forms. An “A” form committed a player to a tryout, the “B” form gave teams the right to sign a player in exchange for a bonus, while a “C” form was usually signed by a player at least 18 years old or by their parents and would give the franchise the rights to that player.

In 1960, a Maple Leafs’ bird-dog scout, Anthony Gilchrist, was the coach of 12-year-old Bobby Orr. He wrote a letter to Maple Leafs GM, Punch Imlach, stating that he should come to watch the young phenom live. In his letter, he said, “It might pay to have one of your men look him over in Barrie and place him on your list before Hap Emms sees him, or I feel sure it will be too late.”

Imlach shrugged the suggestion off and had one of his head scouts, Bob Davidson, reply in writing, saying, “I would like to… thank you for recommending Bob Orr to our organization, but this boy is a little too young to be put on any list for protection. In regard to Emms placing him on a list, the pro clubs cannot put a boy on the list until he is 18 years old.”

Bobby Orr
Bobby Orr. (Photo by Bruce Bennett Studios/Getty Images)

The Bruins greatly benefitted from Imlach’s arrogance, as “Bob Orr” became one of the greatest players ever to lace up skates. Over 50 years later, the thought of Orr in a Maple Leafs jersey doesn’t seem right at all.

Bruins Hand Maple Leafs 11-0 Thrashing

On Jan. 18, 1964, the Bruins beat the Maple Leafs 11-0. After 59 years, it still remains the most-lopsided shutout loss in Maple Leafs’ franchise history.

Forward Dean Prentice, who had a 22-year NHL career spanning from 1952-53 until the 1973-74 season, had three goals and three assists in the blowout victory, while Johnny Bucyk added a goal and three assists of his own. The Bruins scored six goals in the first period alone and never let up, scoring another four in the third period.

Bruins Snag Gerry Cheevers From Maple Leafs

From 1952-1975, the NHL held the Intra-League Draft, which was designed to keep teams relatively competitive during the Original Six era and in the early stages of the expansion era. The team that finished last in the standings in the previous season was awarded the first choice.

Terry Sawchuk, one of the greatest goaltenders in NHL history, was claimed from the Red Wings in 1964. With two veteran goaltenders in Johnny Bowers and Sawchuk, the Maple Leafs opted to leave a 25-year-old Gerry Cheevers available to be claimed in the 1965 Intra-Draft.

Goalie Gerry Cheevers
NEW YORK, NY – 1974: Goalie Gerry Cheevers #30 of the Boston Bruins defends the net during an NHL game against the New York Rangers circa 1974 at the Madison Square Garden in New York, New York. (Photo by B Bennett/Getty Images)

The Bruins, who were in the midst of an eight-season playoff drought, capitalized on the opportunity and claimed Cheevers from the Maple Leafs, who went on to become an iconic goaltender, winning two Stanley Cups in Boston in 1970 and 1972. He was inducted into the Hockey Hall of Fame in 1985 and also was the first goalie to decorate his mask. He famously had stitches painted on his mask where pucks struck the face protector.

Bobby Orr Suffers Initial Knee Injury on Dec. 4, 1966

Orr was one of if not the greatest player in NHL history. Unfortunately, his excellence was cut short due to knee injuries.


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During his rookie season, in 1966-67, he was off to a strong start with 13 points in 18 games leading up to a meeting with the Maple Leafs on Dec. 4, 1966. The star defenceman took a hit from Leafs’ defenceman Marcel Pronovost.

Related: Patrice Bergeron’s Journey From Sitting in the Net to “Mr. Selke”

The hit forced Orr to miss the next seven games and ultimately required knee surgery. Unlike today’s medical technology and knowledge, that first surgery caused Orr more harm than good as he battled through knee problems for the rest of his 12-year career.

Bruins Sweep Maple Leafs During 1969 Playoffs

Having lost four straight playoff series against the Maple Leafs and with a decade in between since the two rivals had last faced off, the Bruins made quick work of the Leafs in the 1969 Quarterfinals.

Phil Esposito Boston Bruins
Phil Esposito, Boston Bruins, circa 1972 (Photo by Bruce Bennett Studios via Getty Images Studios/Getty Images)

Phil Esposito had four goals and two assists during the opening game, which saw the Bruins hand Toronto a 10-0 loss. The Maple Leafs never recovered, as Esposito and the Bruins won the series in four straight games.

Bruins Beat Maple Leafs En Route to 1972 Stanley Cup

The two historic franchises met again during the quarterfinals of the 1972 Stanley Cup Playoffs. In a similar fashion to the sweep in 1969, the Bruins scored a big win in the opening game, beating the Maple Leafs by a score of 5-0. Boston won the series in five games, with nine points apiece through the series, the Bruins’ Esposito (five goals, four assists) and Orr (one goal, eight assists) paved the way for success as the Bruins went on to win the Stanley Cup.

The 1974 Playoffs Marks the Last Series Until 2013

The old rivals met again during the quarterfinals of the 1974 Stanley Cup Playoffs. Sadly, the meeting marked the last playoff battle for 39 years as they didn’t meet again until 2013.

The Bruins made quick work of the Maple Leafs, winning four straight and ultimately went all the way to the Stanley Cup Final. In the Final, they took on the Philadelphia Flyers, losing in a six-game series, but that’s a story for another day.

Darryl Sittler Breaks NHL Record with 10-Point Game

Another memorable moment between the two well-storied franchises came on Feb. 7, 1976, at Maple Leaf Gardens. Unfortunately for the Bruins, they were on the wrong side of this one.

Darryl Sittler Toronto Maple Leafs
Darryl Sittler, Toronto Maple Leafs, circa 1970s (Photo by Bruce Bennett Studios via Getty Images Studios/Getty Images)

Darryl Sittler set an NHL record that may never be broken as he posted 10 points in the Leafs’ 11-4 win over the Bruins. He scored six goals and four assists to etch himself in the NHL record books.

NHL Realignment Cools Rivalry

Following the 1981 NHL realignment, the Maple Leafs were moved to the Western Conference (known as the Campbell Conference at the time) to help minimize travel costs. The move put a dampener on the rivalry as they stayed in the Western Conference until the 1998-99 season.

The Bruins and Maple Leafs rivalry was essentially put on pause. The NHL eventually did the right thing and moved Toronto back into the Eastern Conference making the two teams divisional rivals once again.

Although the Maple Leafs may have gotten the first laugh when looking at the early playoff matchups, the Bruins have definitely gotten the last as they’ve beaten the Leafs every time since moving back to the East.

Bruins and Maple Leafs Rivalry Heating Up Over Past Decade

After many years without playing one another in the postseason, the Bruins have played the Leafs three times over the past decade. Each of their most recent series were highly entertaining matchups and could’ve very well gone either way.

Bruins Make Incredible Comeback in 2013 Stanley Cup Playoffs

Finally, for the first time in 39 years, going back to that 1974 series, the Bruins and Maple Leafs met in the first round of the 2014 Stanley Cup Playoffs. They would require a seventh game to decide the winner.

Karson Kuhlman, Frederik Andersen
Boston Bruins Karson Kuhlman slides through the crease after a save by Toronto Maple Leafs Frederik Andersen. (AP Photo/Charles Krupa)

The Maple Leafs took a 4-1 lead into the third period, and it appeared as though they were going to be moving on to the second round. However, Bruins’ forward, Nathan Horton had different plans as he cut the lead to two midway through the final frame. Milan Lucic and Patrice Bergeron then scored 31 seconds apart with the extra-attacker on the ice to force sudden death. Bergeron followed up his tying-goal heroics by finishing the incredible comeback with the overtime game-winner.

Bruins Win Another 7-Game Series Against Maple Leafs in 2018

Meeting up in the first round in back-to-back seasons, the Bruins and Maple Leafs went to Game 7 in both 2018 and 2019. During Game 1 in 2018, Nazem Kadri made headlines with a bad hit on Bruins’ forward Tommy Wingels. Kadri received a three-game suspension for the play, and the Bruins went on to win the game 5-1.

David Pastrnak joined some elite company in Game 2, picking up three goals and three assists. He joined Esposito and Rick Middleton as the only Bruins to score six points during the postseason. He also became the youngest player in NHL history to record six points in a playoff game, breaking Wayne Gretzky’s previous record. The Bruins took a 2-0 series lead with a 7-3 route of the Maple Leafs.

Boston Bruins David Pastrnak Toronto Maple Leafs Frederik Andersen
Boston Bruins right wing David Pastrnak scores on Toronto Maple Leafs goaltender Frederik Andersen
(THE CANADIAN PRESS/Frank Gunn)

As the series flipped to Toronto, the Maple Leafs were able to win Game 3 before dropping Game 4. With their backs against the ropes, Games 5 and 6 were won by the Maple Leafs, forcing the decisive Game 7.

Heading into Game 7, memories of the epic 2013 collapse flooded the series storylines, and once again the Maple Leafs carried a lead going into the final 20 minutes of the game. In a similar fashion to 2013, the Bruins came alive in the third period, scoring four unanswered goals, winning the game by a final score of 7-4.

Bruins and Maple Leafs Have Rematch in the 2019 Playoffs

The most recent playoff series between the two clubs took place in the 2019 Playoffs. The Maple Leafs, backed by two Mitch Marner goals, won the opener 4-1. Game 2 brought some more controversy, as Kadri once again lost his cool, this time cross-checking Jake DeBrusk in the head. The Maple Leafs were dealt two separate blows, as he was suspended for the remainder of the series, and the Bruins won Game 2.

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Both teams swapped wins in each game going forward, leading up to the third Game 7 between the rivals in just six seasons. This time the Bruins didn’t wait for a dramatic comeback, as they rode an early lead to a 5-1 victory.

Bruins and Maple Leafs By the Numbers

Over the past 100 years, the Bruins have played a total of 767 games against the Maple Leafs. They hold the edge with a regular-season record of 304-269-98-13 and a playoff record of 42-40-1. The one playoff game that finished as a tie was due to Ontario having a Sunday curfew back in 1951, which would have made the game “Illegal” if they had begun another period after midnight.

All in all, the Bruins have played 16 playoff series against the Maple Leafs, with each team winning eight of them. However, the Bruins have won six straight playoff series dating back to the previously mentioned 1969 Quarterfinals.

What the Future Holds for the Rivalry

Both the Bruins and Maple Leafs have undergone some significant changes during the offseason. Toronto parted ways with GM Kyle Dubas and hired Brad Treliving as his replacement. Boston has undergone many roster changes coming off their historic regular season, none more groundbreaking than the announcement that their captain, Bergeron, is retiring.

Patrice Bergeron Boston Bruins
Patrice Bergeron, Boston Bruins (Jess Starr/The Hockey Writers)

Despite all of the changes and the Bruins playing their first season without Bergeron leading the club, they’ll remain a competitive group with a stout defensive unit and one of the best goaltending tandems in the league. The Leafs, although facing some salary cap issues ahead of the season, will also once again be a contending team in the Atlantic, setting up some more good battles in the near future.

Throughout the centennial season, the Bruins will be hosting “Era Nights,” which will honour a specific time period of franchise history. On March 7, while hosting the Maple Leafs, the Bruins will be honouring the franchise from 2001 and beyond in a “Return of the Champion” night. Be sure to mark it on your schedules, as the two Atlantic Division rivals always put on a good show.

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