| Regular season results |
|---|
| No. | R | Date | Score | Opponent | Record |
|---|
| 1 | L | November 6, 1938 | 2–3 | Chicago Black Hawks (1938–39) | 0–1–0 |
| 2 | L | November 10, 1938 | 0–2 | Toronto Maple Leafs (1938–39) | 0–2–0 |
| 3 | L | November 12, 1938 | 1–4 | @ Toronto Maple Leafs (1938–39) | 0–3–0 |
| 4 | L | November 13, 1938 | 3–4 | @ Chicago Black Hawks (1938–39) | 0–4–0 |
| 5 | L | November 17, 1938 | 1–7 | Detroit Red Wings (1938–39) | 0–5–0 |
| 6 | L | November 20, 1938 | 1–2 | @ New York Rangers (1938–39) | 0–6–0 |
| 7 | L | November 22, 1938 | 3–7 | @ New York Americans (1938–39) | 0–7–0 |
| 8 | T | November 24, 1938 | 2–2 OT | New York Americans (1938–39) | 0–7–1 |
| 9 | W | November 27, 1938 | 3–2 | @ Detroit Red Wings (1938–39) | 1–7–1 |
| 10 | W | December 1, 1938 | 2–0 | Boston Bruins (1938–39) | 2–7–1 |
| 11 | W | December 3, 1938 | 3–1 | @ Toronto Maple Leafs (1938–39) | 3–7–1 |
| 12 | L | December 8, 1938 | 5–6 | New York Rangers (1938–39) | 3–8–1 |
| 13 | W | December 11, 1938 | 4–2 | Detroit Red Wings (1938–39) | 4–8–1 |
| 14 | L | December 13, 1938 | 2–3 | @ Boston Bruins (1938–39) | 4–9–1 |
| 15 | L | December 15, 1938 | 0–1 | Boston Bruins (1938–39) | 4–10–1 |
| 16 | L | December 18, 1938 | 2–5 | @ New York Americans (1938–39) | 4–11–1 |
| 17 | L | December 22, 1938 | 2–5 | New York Rangers (1938–39) | 4–12–1 |
| 18 | L | December 25, 1938 | 1–4 | @ Detroit Red Wings (1938–39) | 4–13–1 |
| 19 | L | December 27, 1938 | 1–4 | Chicago Black Hawks (1938–39) | 4–14–1 |
| 20 | W | January 1, 1939 | 4–3 OT | @ Chicago Black Hawks (1938–39) | 5–14–1 |
| 21 | T | January 3, 1939 | 2–2 OT | @ Toronto Maple Leafs (1938–39) | 5–14–2 |
| 22 | T | January 5, 1939 | 2–2 OT | New York Rangers (1938–39) | 5–14–3 |
| 23 | T | January 8, 1939 | 1–1 OT | Detroit Red Wings (1938–39) | 5–14–4 |
| 24 | L | January 10, 1939 | 0–3 | @ Detroit Red Wings (1938–39) | 5–15–4 |
| 25 | L | January 12, 1939 | 4–9 | Toronto Maple Leafs (1938–39) | 5–16–4 |
| 26 | T | January 14, 1939 | 1–1 OT | New York Americans (1938–39) | 5–16–5 |
| 27 | T | January 15, 1939 | 1–1 OT | @ New York Americans (1938–39) | 5–16–6 |
| 28 | W | January 19, 1939 | 1–0 | Boston Bruins (1938–39) | 6–16–6 |
| 29 | L | January 22, 1939 | 3–7 | @ New York Rangers (1938–39) | 6–17–6 |
| 30 | L | January 24, 1939 | 4–6 | @ Boston Bruins (1938–39) | 6–18–6 |
| 31 | W | January 29, 1939 | 1–0 | @ Chicago Black Hawks (1938–39) | 7–18–6 |
| 32 | L | February 2, 1939 | 2–4 | Chicago Black Hawks (1938–39) | 7–19–6 |
| 33 | W | February 9, 1939 | 5–2 | New York Americans (1938–39) | 8–19–6 |
| 34 | T | February 11, 1939 | 3–3 OT | @ Toronto Maple Leafs (1938–39) | 8–19–7 |
| 35 | L | February 12, 1939 | 3–4 | Toronto Maple Leafs (1938–39) | 8–20–7 |
| 36 | L | February 16, 1939 | 1–5 | Boston Bruins (1938–39) | 8–21–7 |
| 37 | W | February 18, 1939 | 7–2 | New York Americans (1938–39) | 9–21–7 |
| 38 | W | February 19, 1939 | 5–4 | @ New York Americans (1938–39) | 10–21–7 |
| 39 | T | February 25, 1939 | 1–1 OT | New York Rangers (1938–39) | 10–21–8 |
| 40 | W | February 26, 1939 | 3–0 | @ New York Rangers (1938–39) | 11–21–8 |
| 41 | L | February 28, 1939 | 2–6 | @ Boston Bruins (1938–39) | 11–22–8 |
| 42 | W | March 2, 1939 | 3–1 | Toronto Maple Leafs (1938–39) | 12–22–8 |
| 43 | W | March 5, 1939 | 2–1 OT | @ Chicago Black Hawks (1938–39) | 13–22–8 |
| 44 | T | March 7, 1939 | 2–2 OT | @ New York Rangers (1938–39) | 13–22–9 |
| 45 | W | March 9, 1939 | 3–2 | Detroit Red Wings (1938–39) | 14–22–9 |
| 46 | L | March 12, 1939 | 1–2 | @ Detroit Red Wings (1938–39) | 14–23–9 |
| 47 | W | March 16, 1939 | 5–1 | Chicago Black Hawks (1938–39) | 15–23–9 |
| 48 | L | March 19, 1939 | 5–7 OT | @ Boston Bruins (1938–39) | 15–24–9 | |
The NHL revised its playoff format and six of seven teams qualified for the playoffs. In the first round, the Canadiens would meet Detroit, which had finished in fifth place. They lost in a best of three series in 3 games, or 1–2.
