Since the 2017–18 season the Canadiens and Maple Leafs have met 41 times in the regular season, and the Maple Leafs have the better of it at 25–16.
Most recently the Canadiens won 3–2 on September 29, 2026.
Right now the Canadiens are 1–1–1 and the Maple Leafs are 2–2–0, with the Canadiens at 8 days since a win against the Maple Leafs' 1.
| Season | Wins |
|---|---|
| 2026–27 | Canadiens 1, Maple Leafs 0 |
| 2025–26 | Canadiens 3, Maple Leafs 1 |
| 2024–25 | Canadiens 1, Maple Leafs 3 |
| 2023–24 | Canadiens 0, Maple Leafs 3 |
| 2022–23 | Canadiens 2, Maple Leafs 2 |
| 2021–22 | Canadiens 2, Maple Leafs 2 |
| 2020–21 | Canadiens 3, Maple Leafs 7 |
| 2019–20 | Canadiens 3, Maple Leafs 0 |
| 2018–19 | Canadiens 1, Maple Leafs 3 |
| 2017–18 | Canadiens 0, Maple Leafs 4 |
| Date | Host | Winner | Score |
|---|---|---|---|
| September 29, 2026 | Maple Leafs home | Canadiens | 3–2 |
| March 10, 2026 | Canadiens home | Canadiens | 3–1 |
| December 6, 2025 | Maple Leafs home | Canadiens | 2–1 |
| November 22, 2025 | Canadiens home | Canadiens | 5–2 |
| October 8, 2025 | Maple Leafs home | Maple Leafs | 5–2 |
| April 12, 2025 | Maple Leafs home | Maple Leafs | 1–0 |
| January 18, 2025 | Canadiens home | Maple Leafs | 7–3 |
| November 9, 2024 | Maple Leafs home | Maple Leafs | 4–1 |
| October 9, 2024 | Canadiens home | Canadiens | 1–0 |
| April 6, 2024 | Canadiens home | Maple Leafs | 4–2 |
| March 9, 2024 | Canadiens home | Maple Leafs | 3–2 |
| October 11, 2023 | Maple Leafs home | Maple Leafs | 6–5 |
| April 8, 2023 | Maple Leafs home | Maple Leafs | 7–1 |
| February 18, 2023 | Maple Leafs home | Maple Leafs | 5–1 |
| January 21, 2023 | Canadiens home | Canadiens | 3–2 |
Full schedules and drought counters: Montreal Canadiens and Toronto Maple Leafs.
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