59 years and counting, as of 2026
1967: The Maple Leafs' Last Stanley Cup
The oldest roster ever to win the Stanley Cup did it in the final season of the NHL's Original Six era — and no Maple Leafs team has managed it since.
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Our sports culture guide mentions the Leafs' championship drought as a running joke across Canada. This page is about the specific night the drought began — and why it's lasted this long.
The last champions of the Original Six
On May 2, 1967, captain George Armstrong scored an empty-net goal to clinch Game 6 against the Montreal Canadiens, giving Toronto a 4–2 series win and its 13th Stanley Cup. It was the final championship of the NHL's "Original Six" era — the 25-year, six-team period from 1942 to 1967 — before the league doubled in size to 12 teams the following season.
The oldest team to ever win it
That 1967 Leafs roster remains the oldest to ever win a Stanley Cup, averaging 31 years old, with goaltender Johnny Bower at 42 and defenceman Allan Stanley at 41 — a genuinely unusual "old guard makes one last run" story, rather than a young team building toward a dynasty.
A drought that's outlived most of the team
The Maple Leafs have not won another Stanley Cup since — a drought that had reached 59 years as of 2026, among the longest active championship droughts in North American professional sports, and a running source of both civic frustration and gallows humour across the country. It's reached the point where the wait itself has become as much a part of the team's identity as any specific era of play.
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Sources
- The Canadian Encyclopedia — Toronto Maple Leafs 1967: The Last Stanley Cup
- NHL.com — 1967 Toronto Maple Leafs Retrospective
- CBC News — Reminiscing With Leafs Fans Who Remember the Team's Last Stanley Cup Win