What’s The Longest Stanley Cup Drought In NHL History? One Team Has Felt More Pain Than Any Other

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One of the harsh realities of being a sports fan is knowing that there’s only so much you can do to avoid the pain and suffering that comes with rooting for a team going through a rebuild or one that spends years seeking a championship only to come up short time and time again.

Most people are willing to stick with those squads through the lowest of lows in the hopes they’ll eventually get to experience the highest of highs that come with watching them finally secure a title.

Unfortunately, that tends to be much easier said than done—and there are plenty of franchises out there who’ve spent decades trying to crack the code without being able to figure out how to put all of the pieces together.

That includes a number of NHL teams that have seen hockey’s ultimate prize—the Stanley Cup—elude them for longer than most of their fans have ever been alive.

That includes a dozen teams who have never been able to win that iconic piece of hardware since joining the NHL—including the Canucks and the Sabres, who are still in search of the trophy after being welcomed into the fold in 1971 (Vancouver has come up short in the Stanley Cup Finals on three occasions, while the Sabres have lost in the last round twice).

However, none of them have anything on the one team that’s experienced the longest Stanley Cup drought ever—one that can be traced back to the year Lyndon B. Johnson was still in the White House, The Graduate was the highest-grossing movie at the box office, and The Andy Griffith Show was the most popular show on television.

What’s the longest Stanley Cup drought in NHL history?

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The fact that the only photos of the celebration that ensued the last time the Maple Leafs won the Stanley Cup are in black-and-white tells you basically everything you need to know about how long it’s been since Toronto earned the right to hoist it.

The Original Six team secured the Stanley Cup for the first time in 1918 and experienced plenty of continued success in the ensuing decades.

The relatively small playing field in the NHL obviously made it a bit easier to win a title toward the middle of the 20th century, but that shouldn’t take away from the fact that the team appeared in the Stanley Cup Finals 22 times between its first win and its most recent one, which transpired when it conquered the Canadiens in 1967 in six games for its 13th title (currently tied for the second of all-time behind Montreal).

Unfortunately, it was all downhill from there.

The Maple Leafs may be the most popular team to call Canada home (which is a major point of contention for fans of other squads in the Great White North that take issue with the amount of coverage the national media devotes to them), but they’ve arguably been the country’s least successful team since winning in 1967.

A Canadian team hasn’t won the Stanley Cup since Montreal did so in 1993, but (with the exception of the relative newcomers who are the Jets) they’ve at least given their supporters some glimmers of hope by appearing in the Stanley Cup Finals on at least one occasion since the start of the new millennium.

The Maple Leafs, on the other, hand, have not only not won a Stanley Cup since 1967 but have not even appeared in the Finals since then, which makes this drought one of the most brutal ones in any professional sport.

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Connor Toole avatar and headshot for BroBible
Connor Toole is the Deputy Editor at BroBible. He is a New England native who went to Boston College and currently resides in Brooklyn, NY. Frequently described as "freakishly tall," he once used his 6'10" frame to sneak in the NBA Draft and convince people he was a member of the Utah Jazz.