No. | R | Date | Score | Opponent | Record |
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1 | W | November 4, 1939 | 5–0 | Boston Bruins (1939–40) | 1–0–0 |
2 | T | November 11, 1939 | 1–1 OT | New York Rangers (1939–40) | 1–0–1 |
3 | W | November 12, 1939 | 1–0 | @ New York Rangers (1939–40) | 2–0–1 |
4 | W | November 18, 1939 | 3–0 | Detroit Red Wings (1939–40) | 3–0–1 |
5 | W | November 19, 1939 | 7–1 | @ Detroit Red Wings (1939–40) | 4–0–1 |
6 | W | November 25, 1939 | 4–3 | New York Americans (1939–40) | 5–0–1 |
7 | L | November 26, 1939 | 1–2 OT | @ New York Americans (1939–40) | 5–1–1 |
8 | L | November 28, 1939 | 2–6 | @ Boston Bruins (1939–40) | 5–2–1 |
9 | T | December 2, 1939 | 3–3 OT | Chicago Black Hawks (1939–40) | 5–2–2 |
10 | W | December 3, 1939 | 3–1 OT | @ Chicago Black Hawks (1939–40) | 6–2–2 |
11 | L | December 7, 1939 | 1–4 | @ Montreal Canadiens (1939–40) | 6–3–2 |
12 | W | December 9, 1939 | 3–0 | Montreal Canadiens (1939–40) | 7–3–2 |
13 | T | December 14, 1939 | 1–1 OT | Boston Bruins (1939–40) | 7–3–3 |
14 | W | December 16, 1939 | 5–1 | New York Americans (1939–40) | 8–3–3 |
15 | W | December 17, 1939 | 4–1 | @ New York Americans (1939–40) | 9–3–3 |
16 | L | December 19, 1939 | 2–3 OT | @ Boston Bruins (1939–40) | 9–4–3 |
17 | L | December 21, 1939 | 1–3 | @ Chicago Black Hawks (1939–40) | 9–5–3 |
18 | W | December 23, 1939 | 5–1 | Detroit Red Wings (1939–40) | 10–5–3 |
19 | L | December 25, 1939 | 1–4 | @ New York Rangers (1939–40) | 10–6–3 |
20 | W | December 28, 1939 | 6–4 | @ Montreal Canadiens (1939–40) | 11–6–3 |
21 | W | December 30, 1939 | 4–2 | Chicago Black Hawks (1939–40) | 12–6–3 |
22 | W | December 31, 1939 | 3–2 | @ Detroit Red Wings (1939–40) | 13–6–3 |
23 | L | January 4, 1940 | 1–2 | @ Chicago Black Hawks (1939–40) | 13–7–3 |
24 | W | January 6, 1940 | 3–1 | Montreal Canadiens (1939–40) | 14–7–3 |
25 | W | January 9, 1940 | 3–2 | @ New York Americans (1939–40) | 15–7–3 |
26 | L | January 11, 1940 | 2–5 | Boston Bruins (1939–40) | 15–8–3 |
27 | L | January 13, 1940 | 1–4 | New York Rangers (1939–40) | 15–9–3 |
28 | T | January 18, 1940 | 2–2 OT | Detroit Red Wings (1939–40) | 15–9–4 |
29 | W | January 20, 1940 | 5–1 | New York Americans (1939–40) | 16–9–4 |
30 | L | January 21, 1940 | 2–3 | @ Detroit Red Wings (1939–40) | 16–10–4 |
31 | L | January 23, 1940 | 1–4 | @ Boston Bruins (1939–40) | 16–11–4 |
32 | L | January 25, 1940 | 0–3 | @ New York Rangers (1939–40) | 16–12–4 |
33 | W | January 27, 1940 | 3–1 | Montreal Canadiens (1939–40) | 17–12–4 |
34 | L | February 3, 1940 | 2–3 | Chicago Black Hawks (1939–40) | 17–13–4 |
35 | L | February 8, 1940 | 1–2 | @ New York Rangers (1939–40) | 17–14–4 |
36 | T | February 10, 1940 | 4–4 OT | New York Rangers (1939–40) | 17–14–5 |
37 | W | February 17, 1940 | 3–1 | Montreal Canadiens (1939–40) | 18–14–5 |
38 | W | February 18, 1940 | 2–1 | @ Montreal Canadiens (1939–40) | 19–14–5 |
39 | L | February 20, 1940 | 0–5 | @ Boston Bruins (1939–40) | 19–15–5 |
40 | W | February 22, 1940 | 2–1 | @ Detroit Red Wings (1939–40) | 20–15–5 |
41 | W | February 24, 1940 | 3–1 | Boston Bruins (1939–40) | 21–15–5 |
42 | W | February 29, 1940 | 3–1 | Detroit Red Wings (1939–40) | 22–15–5 |
43 | T | March 2, 1940 | 1–1 OT | New York Rangers (1939–40) | 22–15–6 |
44 | W | March 9, 1940 | 5–2 | Chicago Black Hawks (1939–40) | 23–15–6 |
45 | L | March 10, 1940 | 1–2 | @ Chicago Black Hawks (1939–40) | 23–16–6 |
46 | W | March 14, 1940 | 8–4 | @ Montreal Canadiens (1939–40) | 24–16–6 |
47 | W | March 16, 1940 | 8–6 | New York Americans (1939–40) | 25–16–6 |
48 | L | March 17, 1940 | 2–5 | @ New York Americans (1939–40) | 25–17–6 | |
The Maple Leafs played the Chicago Black Hawks and Detroit Red Wings in the first two rounds of the playoffs in best of three series, and swept both. In the finals, they played the New York Rangers in a best of seven series and lost 4–2.