Top 5 first round Stanley Cup playoff moments in Boston Bruins history

As the first round of the Stanley Cup Playoffs are heating up and the Boston Bruins are not involved, what better time to take a stroll down memory Causeway Street. The Bruins have made the playoffs in 77 of 100 seasons, second only to the rival Montreal Canadiens (86 appearances), so we have a lot of history to sort through. Here are my top five first round moments in Boston Bruins history.

#5. 2008 — Bruins Force Game 7 Against Montreal

In 2008, a young Bruins squad, led by players like Phil Kessel, Milan Lucic, and Zdeno Chara, faced off against the rival Montreal Canadiens. Despite falling behind 3-1 in the series, the Bruins roared back to force a dramatic Game 7 after an electrifying 5-4 win at home. Although they ultimately lost the series, this was a turning point — the arrival of the modern-era Bruins. It proved that Boston’s young core could battle with the NHL’s best and set the stage for their eventual dominance in the years to come.

#4. 1988 — Bruins Defeat the Montreal Canadiens (Finally)

For 45 years, the Bruins had tried — and failed — to defeat the Canadiens in the playoffs.
Eighteen straight series losses stretched all the way back to the days of Maurice Richard.
In 1988, everything changed. Led by Cam Neely, Ray Bourque, and Andy Moog, Boston finally broke the curse, defeating Montreal 4–1 in the series.It was a moment of pure relief for the franchise and its fans — finally slaying their greatest rival.

#3. 1983 — Rick Middleton Dominates Against Buffalo

Few playoff performances in Bruins history are as quietly legendary as Rick Middleton’s 1983 first-round series against the Buffalo Sabres. Middleton scored a mind-boggling 19 points in the seven games, torching Buffalo's defense and goaltending, leading them to a 4-3 series victory. His 5 goals and 14 assists for 19 points are the most points in a single series in NHL history — and yet it often flies under the radar today.

#2. 2011 — Michael Ryder’s Save and Nathan Horton’s Game Winner Against Montreal

The 2011 Bruins faced an all-out war with Montreal in the first round, and the defining moments came in Game 5 and Game 7. First, Michael Ryder, a forward, not a goalie, made an unbelievable glove save on the goal line to preserve a tie. Then, in a classic Game 7 at TD Garden, Nathan Horton scored the series-clinching overtime goal, sending the Bruins forward on their Cup-winning journey. Grit, guts, and greatness all wrapped into one unforgettable series.

#1. 2013 — Game 7 Comeback vs Toronto

There’s playoff drama —and then there’s 2013 Bruins vs Leafs.
Down 4–1 midway through the third period of Game 7, the Bruins launched one of the greatest comebacks in NHL history. Goals from Nathan Horton, Milan Lucic, and Patrice Bergeron tied the game in the final minute. Then, fittingly, Bergeron capped it off in overtime, sending the Garden into absolute pandemonium. It propelled the Bruins on a run all the way to the Stanley Cup Finals, and in my opinion is the greatest first round moment in franchise history.