| No. |
R |
Date |
Score |
Opponent |
Record |
| 1 | L | October 8, 1959 | 1–4 | @ Montreal Canadiens (1959–60) | 0–1–0 |
| 2 | W | October 10, 1959 | 6–4 | New York Rangers (1959–60) | 1–1–0 |
| 3 | W | October 11, 1959 | 8–4 | Montreal Canadiens (1959–60) | 2–1–0 |
| 4 | W | October 14, 1959 | 4–3 | @ New York Rangers (1959–60) | 3–1–0 |
| 5 | L | October 17, 1959 | 0–3 | @ Toronto Maple Leafs (1959–60) | 3–2–0 |
| 6 | T | October 18, 1959 | 2–2 | @ Chicago Black Hawks (1959–60) | 3–2–1 |
| 7 | L | October 22, 1959 | 1–4 | @ Detroit Red Wings (1959–60) | 3–3–1 |
| 8 | L | October 24, 1959 | 1–5 | @ Montreal Canadiens (1959–60) | 3–4–1 |
| 9 | W | October 29, 1959 | 2–1 | Detroit Red Wings (1959–60) | 4–4–1 |
| 10 | L | October 31, 1959 | 3–4 | @ Toronto Maple Leafs (1959–60) | 4–5–1 |
| 11 | W | November 1, 1959 | 6–3 | Toronto Maple Leafs (1959–60) | 5–5–1 |
| 12 | W | November 3, 1959 | 6–3 | @ Chicago Black Hawks (1959–60) | 6–5–1 |
| 13 | W | November 5, 1959 | 8–3 | @ Detroit Red Wings (1959–60) | 7–5–1 |
| 14 | W | November 8, 1959 | 5–3 | Chicago Black Hawks (1959–60) | 8–5–1 |
| 15 | L | November 11, 1959 | 3–6 | @ New York Rangers (1959–60) | 8–6–1 |
| 16 | L | November 12, 1959 | 5–6 | Detroit Red Wings (1959–60) | 8–7–1 |
| 17 | L | November 14, 1959 | 1–8 | @ Montreal Canadiens (1959–60) | 8–8–1 |
| 18 | L | November 15, 1959 | 1–4 | Montreal Canadiens (1959–60) | 8–9–1 |
| 19 | T | November 21, 1959 | 3–3 | Detroit Red Wings (1959–60) | 8–9–2 |
| 20 | L | November 22, 1959 | 1–2 | Toronto Maple Leafs (1959–60) | 8–10–2 |
| 21 | T | November 25, 1959 | 3–3 | @ New York Rangers (1959–60) | 8–10–3 |
| 22 | W | November 26, 1959 | 4–3 | New York Rangers (1959–60) | 9–10–3 |
| 23 | T | November 28, 1959 | 2–2 | @ Toronto Maple Leafs (1959–60) | 9–10–4 |
| 24 | L | November 29, 1959 | 2–4 | Montreal Canadiens (1959–60) | 9–11–4 |
| 25 | T | December 2, 1959 | 2–2 | @ Chicago Black Hawks (1959–60) | 9–11–5 |
| 26 | L | December 5, 1959 | 3–4 | @ Detroit Red Wings (1959–60) | 9–12–5 |
| 27 | L | December 6, 1959 | 3–6 | Chicago Black Hawks (1959–60) | 9–13–5 |
| 28 | W | December 10, 1959 | 6–3 | Toronto Maple Leafs (1959–60) | 10–13–5 |
| 29 | L | December 12, 1959 | 3–4 | New York Rangers (1959–60) | 10–14–5 |
| 30 | L | December 13, 1959 | 3–4 | @ New York Rangers (1959–60) | 10–15–5 |
| 31 | L | December 16, 1959 | 0–4 | @ Chicago Black Hawks (1959–60) | 10–16–5 |
| 32 | L | December 20, 1959 | 2–4 | Detroit Red Wings (1959–60) | 10–17–5 |
| 33 | W | December 25, 1959 | 5–1 | Chicago Black Hawks (1959–60) | 11–17–5 |
| 34 | L | December 27, 1959 | 1–6 | @ Chicago Black Hawks (1959–60) | 11–18–5 |
| 35 | W | December 29, 1959 | 4–3 | @ New York Rangers (1959–60) | 12–18–5 |
| 36 | W | January 1, 1960 | 7–3 | New York Rangers (1959–60) | 13–18–5 |
| 37 | L | January 2, 1960 | 5–6 | @ Montreal Canadiens (1959–60) | 13–19–5 |
| 38 | L | January 3, 1960 | 3–4 | @ Detroit Red Wings (1959–60) | 13–20–5 |
| 39 | W | January 7, 1960 | 5–1 | Chicago Black Hawks (1959–60) | 14–20–5 |
| 40 | W | January 9, 1960 | 3–2 | @ Toronto Maple Leafs (1959–60) | 15–20–5 |
| 41 | W | January 10, 1960 | 4–0 | Toronto Maple Leafs (1959–60) | 16–20–5 |
| 42 | W | January 14, 1960 | 6–0 | New York Rangers (1959–60) | 17–20–5 |
| 43 | L | January 16, 1960 | 2–8 | @ Montreal Canadiens (1959–60) | 17–21–5 |
| 44 | L | January 17, 1960 | 1–3 | Montreal Canadiens (1959–60) | 17–22–5 |
| 45 | L | January 20, 1960 | 1–3 | @ Chicago Black Hawks (1959–60) | 17–23–5 |
| 46 | L | January 21, 1960 | 2–5 | @ Detroit Red Wings (1959–60) | 17–24–5 |
| 47 | T | January 23, 1960 | 3–3 | @ Toronto Maple Leafs (1959–60) | 17–24–6 |
| 48 | W | January 24, 1960 | 6–2 | Toronto Maple Leafs (1959–60) | 18–24–6 |
| 49 | W | January 30, 1960 | 3–2 | Detroit Red Wings (1959–60) | 19–24–6 |
| 50 | W | January 31, 1960 | 6–5 | Montreal Canadiens (1959–60) | 20–24–6 |
| 51 | L | February 4, 1960 | 2–7 | Chicago Black Hawks (1959–60) | 20–25–6 |
| 52 | L | February 6, 1960 | 3–5 | @ Montreal Canadiens (1959–60) | 20–26–6 |
| 53 | W | February 7, 1960 | 3–0 | Toronto Maple Leafs (1959–60) | 21–26–6 |
| 54 | W | February 11, 1960 | 3–2 | Detroit Red Wings (1959–60) | 22–26–6 |
| 55 | W | February 13, 1960 | 7–6 | Montreal Canadiens (1959–60) | 23–26–6 |
| 56 | W | February 14, 1960 | 3–0 | New York Rangers (1959–60) | 24–26–6 |
| 57 | L | February 17, 1960 | 1–3 | @ Toronto Maple Leafs (1959–60) | 24–27–6 |
| 58 | L | February 20, 1960 | 1–4 | @ Detroit Red Wings (1959–60) | 24–28–6 |
| 59 | L | February 21, 1960 | 2–7 | @ New York Rangers (1959–60) | 24–29–6 |
| 60 | W | February 27, 1960 | 3–1 | @ Chicago Black Hawks (1959–60) | 25–29–6 |
| 61 | L | March 1, 1960 | 2–3 | @ Detroit Red Wings (1959–60) | 25–30–6 |
| 62 | L | March 3, 1960 | 0–2 | Chicago Black Hawks (1959–60) | 25–31–6 |
| 63 | L | March 5, 1960 | 2–5 | @ Toronto Maple Leafs (1959–60) | 25–32–6 |
| 64 | L | March 6, 1960 | 1–3 | Toronto Maple Leafs (1959–60) | 25–33–6 |
| 65 | T | March 10, 1960 | 3–3 | New York Rangers (1959–60) | 25–33–7 |
| 66 | W | March 12, 1960 | 5–1 | Detroit Red Wings (1959–60) | 26–33–7 |
| 67 | W | March 13, 1960 | 3–2 | Montreal Canadiens (1959–60) | 27–33–7 |
| 68 | W | March 16, 1960 | 3–2 | @ New York Rangers (1959–60) | 28–33–7 |
| 69 | L | March 19, 1960 | 1–5 | @ Montreal Canadiens (1959–60) | 28–34–7 |
| 70 | T | March 20, 1960 | 5–5 | Chicago Black Hawks (1959–60) | 28–34–8 |