When was the last time Toronto Maple Leafs beat the Boston Bruins in a playoff series?

The Toronto Maple Leafs and the Boston Bruins are facing off in the first round of the 2023-24 Stanley Cup playoffs. The two teams have a storied playoff history dating back to the early years of the NHL.

To date, the Leafs and the Bruins have met a total of 16 times in the playoffs, but the last victory for the Maple Leafs dates back to 1959.

The two teams have split the 16 series. The Leafs won the first series in 1932-33 and registered four consecutive series victories. However, the Bruins snapped this streak by securing a win in the 1938-39 series.

The last time the Toronto Maple Leafs tasted victory in a playoff series against the Bruins was in 1958-59, when they won 4-3. Leafs’ Gary Ehman delivered the series-deciding winner in the final three minutes of game seven.

That season, they advanced to the Stanley Cup Finals but lost to the Montreal Canadiens.

Despite their success against the Bruins in the early years, the Maple Leafs have struggled to replicate that dominance in recent decades.

The most recent playoff showdown between the two teams took place in 2019, with the Bruins coming out victorious in a hard-fought seven-game series.

This defeat was particularly bitter for Leafs fans, as it marked their sixth consecutive playoff series loss to the Bruins.

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Toronto Maple Leafs to break 65-year playoff series win-drought against Bruins?

Toronto Maple Leafs v Boston Bruins - Game One

As bitter as it sounds, the Toronto Maple Leafs haven’t won a playoff series against the Bruins for 65 years.

This season could be a good opportunity for Toronto to break this ominous streak, but its regular season record against the Bruins wasn't too bright. The Bruins won all four meetings against the Maple Leafs, outscoring them 14-7.

In their last playoff meeting in 2019, the Boston Bruins once again proved to be the better team, ending the Maple Leafs' postseason aspirations for another year. But things could change this year with the Maple Leafs undergoing significant changes in their roster and management since their last playoff series against the Bruins.