Key dates of the season, the most common bets on the Maple Leafs and what to know depending on your province.
Not offered in Ontario or Alberta. 18+ or 19+ depending on province.
| Arena | Scotiabank Arena, Toronto |
|---|---|
| Stanley Cups | 13 — the last in 1967 |
| First game 2026-27 | September 29, against the Montreal Canadiens |
| Worth watching | The expected debut of Gavin McKenna, the first overall pick |
The Maple Leafs opened 2026-27 at home against the Canadiens, with the much-awaited debut of first overall pick Gavin McKenna. Toronto’s drought since 1967 comes up in every conversation about Stanley Cup odds.
Like every team, Toronto plays 84 games this season instead of 82: 42 at Scotiabank Arena, 42 on the road. The official schedule includes 11 back-to-backs.
| Date | Game | Why it matters |
|---|---|---|
| September 29-30, 2026 | Canadiens, then Islanders, in Toronto | NHL opening night, followed by a second game the next night |
| October 8-13, 2026 | Vegas, Colorado, Utah | First road trip (3 games) |
| October 24-31, 2026 | Edmonton, Calgary, Seattle, Vancouver | Western swing (4 games) |
| November 7, 2026 | Canadiens in Toronto | Second game against the Habs, New Jersey the next night |
| December 22, 2026 to January 7, 2027 | Detroit, Montreal, Anaheim, Los Angeles, San Jose, Washington, Philadelphia | Longest road stretch (7 games), including Montreal on December 26 |
| March 22, 2027 | Leafs at Montreal | Fourth game against the Habs |
| April 10, 2027 | Leafs at the Rangers | Regular-season finale |
Toronto went 32-36-14 in 2025-26, finished last in the Atlantic and missed the playoffs. Management, the coach and a good part of the roster have changed since.
These are things to check, not a winning system.
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See also: NHL guide · Canadiens · Oilers · Canucks · Jets · Flames · Senators · province checker
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Sources: NHL: 2026-27 regular-season schedule · NHL: Gavin McKenna drafted No. 1 by Toronto · Maple Leafs: 2026-27 schedule · NHL: Berube fired · Maple Leafs: Jim Hiller named head coach · TSN: Bobrovsky and the July 1 additions · NHL: Maple Leafs season preview 2026-27 · TSN: Matthews injury (March 2026) · Maple Leafs: Matthews at camp (Sept. 18, 2026) · Maple Leafs: McKenna entry-level contract
September 29, 2026, at home against the Montreal Canadiens.
No. Our operators aren't offered in Ontario or Alberta; fans in other provinces can bet with them.
Jim Hiller, hired on June 17, 2026. He replaced Craig Berube, who was fired on May 13, 2026 after a season without playoffs.
In 1967. It was the 13th Stanley Cup in franchise history.
Four times: September 29, 2026 and November 7, 2026 in Toronto, then December 26, 2026 and March 22, 2027 in Montreal.
84 regular-season games: 42 at home and 42 on the road. The finale is scheduled for April 10, 2027 against the Rangers in New York.