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The Toronto Maple Leafs and Boston Bruins are two of the oldest surviving franchises from the NHL’s first decade, yet somehow they have only met sixteen times in the playoffs over the past 106 seasons. While the overall playoff results have the teams tied 8-8 in series wins, all of those wins are in our grandparents’ past, as the Maple Leafs have not beaten the Bruins in a playoff series since the 1950s. Expansion hurts us all. That and passing on Bobby Orr.

1932-33: Toronto Maple Leafs over Boston Bruins in five games - 3-2

The first time these two franchises faced off, the Maple Leafs took the five game semi-final series all the way to the limit, winning in game five. The season’s series was heavily in Boston’s favour, with the Maple Leafs going 1-4-1 against the Bruins. The most noteworthy game is game five, which went to triple overtime and is the second longest game in NHL history.

After defeating the Bruins in the semi-finals, the Maple Leafs would fall three games to one to the New York Rangers in the Stanley Cup Final.

I’m going to take a minute and just ponder here why the Maple Leafs and Bruins were the only series in the 1933 postseason to play a best of five series versus a total goals series like every other series aside from the Stanley Cup Finals. NHL, what were you doing?

1934-35: Toronto Maple Leafs over Boston Bruins in four games - 3-1

Two years later they met again, and the Bruins again won the season series 3-2-1. In the playoffs, however, the Maple Leafs beat the Bruins in four games this time around. The end result was the same however, with a Stanley Cup Final loss, this time to the Montreal Maroons. This would be the Maroons final Stanley Cup win.

This series featured three shutouts (2 Toronto, 1 Boston) and a double overtime win by Boston in game one.

1935-36: Toronto Maple Leafs over Boston Bruins 8-6 total goals series

The Maple Leafs had the winning record vs the Bruins this time around, going 3-1-2 against Boston. To get into the playoffs the Maple Leafs had to play a two game total goal series against the Bruins. The Maple Leafs won this series 8-6, scoring eight goals against the Bruins at Boston Garden in game two.

The Maple Leafs would go on to defeat the New York Americans 2-1 in the semi-finals and go down 3-1 in the Stanley Cup Final against the Detroit Red Wings.

The Maple Leafs 8 goal game featured a hat trick by Charlie Conacher, the second goal being the game winner.

1937-38: Toronto Maple Leafs over Boston Bruins 3-0 in best of five

The Leafs went back to having a losing record against the Bruins at 1-5-2 over the regular season. It wouldn’t matter though, as the Leafs swept the Bruins in three games in round one, but would lose 3-1 to the Chicago Black Hawks in the finals.

The sweep included one double overtime shutout and a 3-2 overtime win at the Boston Garden.

1938-39: Boston Bruins over Toronto Maple Leafs 4-1 in the Stanley Cup Final

The Bruins would finally defeat the Maple Leafs when it mattered the most. The Maple Leafs beat the New York Americans (2-0) and the Detroit Red Wings (2-1) on their way to the finals, but couldn’t top Boston this time as the Bruins would win their second Stanley Cup in five games.

The Maple Leafs only win of the series came in overtime, after the Bruins rallied back from an early 2-0 deficit.

1940-41: Boston Bruins over Toronto Maple Leafs 4-3

Two playoff wins in a row for the Bruins, as they beat the Leafs in a tough seven game series in the semi-finals. The Bruins would move on to sweep the Detroit Red Wings in the finals for Stanley Cup #3.

Game seven was a close contest, tied 1-1 midway through the first period and then Mel Hill scored the winning goal for the Bruins with five minutes left to go.

1947-48: Toronto Maple Leafs over Boston Bruins 4-1

The Maple Leafs would have to wait eight years for their revenge, and they would make quick work of the Bruins in the semi-finals before dispatching of the Red Wings in a four game sweep for their seventh Stanley Cup.

Game five was a big 5-1 win for the Leafs in Boston that saw Bill Barilko, Howie Meeker, Ted Kennedy, Garth Beosch, and Nick Metz score for Toronto.

1948-49: Toronto Maple Leafs over Boston Bruins 4-1

A perfect repeat of the 1948 playoffs, the Leafs defeated the Bruins in five games and went on to sweep the Red Wings in the Cup final.

Game three was the big one again, which saw the Bruins win 5-4 in overtime at Maple Leaf Gardens. Woody Dumart scored the overtime goal with just under four minutes remaining, allowing the players to get to bed at a decent time for their day jobs.

1950-51: Toronto Maple Leafs over Boston Bruins 4-1

Another five game series victory for the Leafs in the semi-finals and then they would go on to beat the Montreal Canadiens for the cup in another five game series.

The series winner was a big 6-0 win with Joe Klukay scoring three points (2G, 1A).

1958-59: Toronto Maple Leafs over Boston Bruins 4-3

After almost a decade apart from each other, they found a way to play again. In the semi-finals we have another Bruins defeat, this time the series went all the way to seven games, with the Leafs coming out on top.  Unfortunately, the Maple Leafs would fall to the Montreal Canadiens in five games in the Stanley Cup Final.

This series had two overtime games and would be won in a 3-2 victory for Toronto by a goal with under 3 minutes left by Gary Ehman.

1968-69: Boston Bruins over Toronto Maple Leafs 4-0

A decade after their last meeting, the Maple Leafs lost their playoff mojo against the Bruins, being swept in the quarter-finals. Including two big blowouts of 10-0 and 7-0.

The goalies subjected to those blowouts were Johnny Bower and Bruce Gamble; they did alright otherwise in their careers, though.

1971-72: Boston Bruins over Toronto Maple Leafs 4-1

The first-overall Bruins finished the season 39 points (119)  ahead of the Maple Leafs (80). What followed was an easy four wins - and one OT loss - over the Maple Leafs enroute to winning their fifth Stanley Cup over the New York Rangers.

The only winning goal for Toronto came in overtime and was scored by Jim Harrison.

1973-74: Boston Bruins over Toronto Maple Leafs 4-0

The Bruins again finished first overall in the NHL and used their might to again eliminate the Maple Leafs in the first round. The Bruins wouldn’t get a sixth Stanley Cup however, as they would fall to the Philadelphia Flyers in six games.

The Leafs made a game of it in game seven, losing 4-3 in overtime after Inge Hammarstrom tied the game with 1:47 left in the third period.

2013: Boston Bruins over Toronto Maple Leafs 4-3

We all know this series, as the final 15 minutes are ingrained in our minds. This is where the phrase ‘It was 4-1’ was born. It was supposed to be the highlight for the Brian Burke built Maple Leafs – though Burke himself was relieved of the General Manager position just days before the season began. However, one miracle comeback by the Bruins (that Bruins owner Jeremy Jacobs didn’t see; he left the game assuming that the Bruins were eliminated), and we were left stunned with the image of James Reimer lying face down in his crease. Most Leafs fans have made peace with the loss, and would kindly like everyone to shut up about it.

2018: Boston Bruins over Toronto Maple Leafs 4-3

After a five season gap, the Leafs and Bruins faced off again for the fifteenth time in the two franchises history. The Bruins would win games one (5-1) and two (7-3) easily, and the Maple Leafs would lose centre Nazem Kadri to a three game suspension for a hit on Tommy Wingels. The Maple Leafs would make up some ground in game three (4-2), and win games five (4-3)and six (3-1) to overcome a 3-1 series deficit after dropping game four (3-1) on home ice. Game seven saw the Maple Leafs take a 4-3 lead into the third period, but then give the game away to the Bruins who scored four goals in the third period to win the game 7-4.

2019: Boston Bruins over Toronto Maple Leafs 4-3

Back to back playoff series against the Bruins had everyone hoping for a redemption story, but two things repeated. The Bruins won, and Nazem Kadri was suspended. The Maple Leafs came out strong with a 4-1 win in the Toronto Dominion Garden, but lost by the same score in the second game. In fact, both teams would trade wins each game, with the Leafs squeaking out close wins in games three (3-2) and five (2-1) and the Bruins won games four (6-4) and six (4-2) with bigger scores and a two goal margin, thanks to empty net goals. Everyone was hoping the pattern would repeat itself in game seven, but the Bruins would jump out to a two goal lead, and lead 3-1 into the third period when Boston would pot two empty net goals to take the series with a 5-1 win.

Sixteen playoff series. Eight straight wins. Eight straight losses.

Toronto's top players have grown since that last series. Boston's top players have aged, retired, and been replaced since that last series.

The Maple Leafs depth has been almost completely overhauled since then.

Will this be the end of the Bruins playoff win streak?

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