2008–09 Toronto Maple Leafs season Game log October

| Game | Date_ | Opponent | Score | Location_ | Attendance | Record | Points |
|---|---|---|---|---|---|---|---|
| 1 | October 9, 2008 | @ Detroit Red Wings | 3–2 | Joe Louis Arena | 20066 | 1–0–0 | 2 |
| 2 | October 11, 2008 | Montreal Canadiens | 1–6 | Air Canada Centre | 19370 | 1–1–0 | 2 |
| 3 | October 13, 2008 | St. Louis Blues | 4–5 (SO) | Air Canada Centre | 19045 | 1–1–1 | 3 |
| 4 | October 17, 2008 | @ New York Rangers | 0–1 (SO) | Madison Square Garden | 18200 | 1–1–2 | 4 |
| 5 | October 18, 2008 | @ Pittsburgh Penguins | 1–4 | Mellon Arena | 17033 | 1–2–2 | 4 |
| 6 | October 21, 2008 | Anaheim Ducks | 2–3 (SO) | Air Canada Centre | 19222 | 1–2–3 | 5 |
| 7 | October 23, 2008 | @ Boston Bruins | 4–2 | TD Banknorth Garden | 12274 | 2–2–3 | 7 |