The series began on December 3, 1924, when the Toronto St. Patricks (renamed Maple Leafs in 1927) met the Boston Bruins for the first time.

The Bruins played their first Stanley Cup playoff series against the Maple Leafs following the 1932–33 NHL season.

[1] This occurred after Maple Leafs teammate King Clancy upended Shore with a hard check as the later player rushed up the ice.

[5] An all-star benefit game was held at Maple Leaf Gardens on February 14, 1934, which raised $20,909 for Bailey and his family.

Game one at the Boston Garden was a 10–0 blowout, where Maple Leafs defenceman Pat Quinn bodychecked the Bruins' Bobby Orr in open-ice, knocking him out and leading to a bench-clearing brawl.

However, before playing a regular season game for Toronto, he was traded to the Bruins in exchange for former Calder Memorial Trophy-winning goaltender Andrew Raycroft.

Toronto management had deemed Justin Pogge their potential goaltender of the future, rendering Rask expendable.

The Bruins rallied from a 4–1 third period deficit to defeat the Maple Leafs in overtime, 5–4, and advance to the second round.

[21] In the 2018 Stanley Cup playoffs, Boston Bruins again defeated Toronto Maple Leafs in seven games.

[26] In game five, Toronto prevented a come-back by Boston, fending off the Bruins 4–3 as Frederik Andersen made 42 saves for the Maple Leafs.

[28] In game seven, Bruins forward Patrice Bergeron scored a goal and recorded two assists in a 7–4 victory to advance his team to the second round.

[34] In Game three, both Auston Matthews and Andreas Johnsson scored a goal and notched an assist, leading the Maple Leafs to a 3–2 victory.

[35] In Game four, the Bruins held onto a 6–4 victory keeping the Maple Leafs from tying in the dying minutes after leading by three goals in the third period.

[38] In the seventh game, Rask made 32 saves to defeat the Maple Leafs 5–1 and advance to the second round.