| No. | R | Date | Score | Opponent | Record | 
| 1 | L | October 11, 1958 | 1–3 | Chicago Black Hawks (1958–59) | 0–1–0 | 
| 2 | L | October 12, 1958 | 2–5 | @ Chicago Black Hawks (1958–59) | 0–2–0 | 
| 3 | L | October 16, 1958 | 3–4 | @ Montreal Canadiens (1958–59) | 0–3–0 | 
 
| 4 | W | October 18, 1958 | 3–2 | Boston Bruins (1958–59) | 1–3–0 | 
| 5 | L | October 19, 1958 | 1–3 | @ Detroit Red Wings (1958–59) | 1–4–0 | 
 
| 6 | W | October 25, 1958 | 3–0 | Detroit Red Wings (1958–59) | 2–4–0 | 
| 7 | L | October 26, 1958 | 2–3 | @ New York Rangers (1958–59) | 2–5–0 | 
| 8 | L | October 29, 1958 | 0–5 | Montreal Canadiens (1958–59) | 2–6–0 | 
 
| 9 | W | November 1, 1958 | 4–3 | New York Rangers (1958–59) | 3–6–0 | 
| 10 | L | November 2, 1958 | 0–2 | @ Boston Bruins (1958–59) | 3–7–0 | 
 
| 11 | W | November 8, 1958 | 5–3 | Boston Bruins (1958–59) | 4–7–0 | 
 
| 12 | W | November 9, 1958 | 2–0 | @ Detroit Red Wings (1958–59) | 5–7–0 | 
| 13 | L | November 12, 1958 | 1–4 | Montreal Canadiens (1958–59) | 5–8–0 | 
| 14 | L | November 15, 1958 | 1–4 | Detroit Red Wings (1958–59) | 5–9–0 | 
 
| 15 | T | November 16, 1958 | 4–4 | @ Boston Bruins (1958–59) | 5–9–1 | 
| 16 | L | November 19, 1958 | 4–7 | @ New York Rangers (1958–59) | 5–10–1 | 
 
| 17 | T | November 22, 1958 | 2–2 | New York Rangers (1958–59) | 5–10–2 | 
 
| 18 | T | November 23, 1958 | 3–3 | @ Chicago Black Hawks (1958–59) | 5–10–3 | 
| 19 | L | November 26, 1958 | 2–5 | Detroit Red Wings (1958–59) | 5–11–3 | 
| 20 | L | November 27, 1958 | 2–3 | @ Detroit Red Wings (1958–59) | 5–12–3 | 
| 21 | L | November 29, 1958 | 1–2 | Chicago Black Hawks (1958–59) | 5–13–3 | 
 
| 22 | W | November 30, 1958 | 2–1 | @ Boston Bruins (1958–59) | 6–13–3 | 
 
| 23 | T | December 4, 1958 | 2–2 | @ Montreal Canadiens (1958–59) | 6–13–4 | 
 
| 24 | W | December 6, 1958 | 4–1 | Boston Bruins (1958–59) | 7–13–4 | 
 
| 25 | W | December 7, 1958 | 2–0 | @ New York Rangers (1958–59) | 8–13–4 | 
 
| 26 | T | December 10, 1958 | 2–2 | @ Chicago Black Hawks (1958–59) | 8–13–5 | 
 
| 27 | T | December 13, 1958 | 4–4 | New York Rangers (1958–59) | 8–13–6 | 
| 28 | L | December 14, 1958 | 3–6 | @ Boston Bruins (1958–59) | 8–14–6 | 
| 29 | L | December 18, 1958 | 1–4 | @ Montreal Canadiens (1958–59) | 8–15–6 | 
 
| 30 | T | December 20, 1958 | 2–2 | Boston Bruins (1958–59) | 8–15–7 | 
| 31 | L | December 21, 1958 | 1–5 | @ New York Rangers (1958–59) | 8–16–7 | 
 
| 32 | W | December 25, 1958 | 2–0 | @ Detroit Red Wings (1958–59) | 9–16–7 | 
 
| 33 | T | December 27, 1958 | 2–2 | Chicago Black Hawks (1958–59) | 9–16–8 | 
| 34 | L | December 28, 1958 | 3–4 | @ Chicago Black Hawks (1958–59) | 9–17–8 | 
 
| 35 | W | December 31, 1958 | 2–0 | Montreal Canadiens (1958–59) | 10–17–8 | 
| 36 | L | January 3, 1959 | 1–2 | Chicago Black Hawks (1958–59) | 10–18–8 | 
 
| 37 | W | January 4, 1959 | 4–2 | @ New York Rangers (1958–59) | 11–18–8 | 
 
| 38 | W | January 7, 1959 | 3–1 | Detroit Red Wings (1958–59) | 12–18–8 | 
| 39 | L | January 8, 1959 | 0–3 | @ Montreal Canadiens (1958–59) | 12–19–8 | 
 
| 40 | W | January 10, 1959 | 4–1 | Boston Bruins (1958–59) | 13–19–8 | 
 
| 41 | T | January 11, 1959 | 6–6 | @ Detroit Red Wings (1958–59) | 13–19–9 | 
| 42 | L | January 14, 1959 | 2–3 | New York Rangers (1958–59) | 13–20–9 | 
 
| 43 | W | January 17, 1959 | 2–1 | Detroit Red Wings (1958–59) | 14–20–9 | 
| 44 | L | January 18, 1959 | 3–4 | @ Boston Bruins (1958–59) | 14–21–9 | 
 
| 45 | W | January 21, 1959 | 3–1 | Montreal Canadiens (1958–59) | 15–21–9 | 
| 46 | L | January 24, 1959 | 1–3 | Boston Bruins (1958–59) | 15–22–9 | 
 
| 47 | W | January 25, 1959 | 4–1 | @ Chicago Black Hawks (1958–59) | 16–22–9 | 
| 48 | L | January 31, 1959 | 2–5 | New York Rangers (1958–59) | 16–23–9 | 
| 49 | L | February 1, 1959 | 4–6 | @ Boston Bruins (1958–59) | 16–24–9 | 
 
| 50 | W | February 5, 1959 | 6–3 | @ Montreal Canadiens (1958–59) | 17–24–9 | 
 
| 51 | W | February 7, 1959 | 4–1 | Detroit Red Wings (1958–59) | 18–24–9 | 
| 52 | L | February 8, 1959 | 2–7 | @ Chicago Black Hawks (1958–59) | 18–25–9 | 
| 53 | L | February 11, 1959 | 2–5 | Montreal Canadiens (1958–59) | 18–26–9 | 
 
| 54 | W | February 14, 1959 | 5–1 | Chicago Black Hawks (1958–59) | 19–26–9 | 
| 55 | L | February 15, 1959 | 2–4 | @ Detroit Red Wings (1958–59) | 19–27–9 | 
 
| 56 | T | February 21, 1959 | 1–1 | New York Rangers (1958–59) | 19–27–10 | 
| 57 | L | February 22, 1959 | 1–5 | @ Chicago Black Hawks (1958–59) | 19–28–10 | 
 
| 58 | W | February 25, 1959 | 3–2 | Montreal Canadiens (1958–59) | 20–28–10 | 
| 59 | L | February 28, 1959 | 2–4 | Detroit Red Wings (1958–59) | 20–29–10 | 
 
| 60 | T | March 1, 1959 | 1–1 | @ New York Rangers (1958–59) | 20–29–11 | 
 
| 61 | W | March 4, 1959 | 5–2 | Chicago Black Hawks (1958–59) | 21–29–11 | 
| 62 | L | March 5, 1959 | 1–2 | @ Montreal Canadiens (1958–59) | 21–30–11 | 
 
| 63 | W | March 7, 1959 | 4–1 | Boston Bruins (1958–59) | 22–30–11 | 
| 64 | L | March 8, 1959 | 3–4 | @ Boston Bruins (1958–59) | 22–31–11 | 
| 65 | L | March 11, 1959 | 2–6 | Montreal Canadiens (1958–59) | 22–32–11 | 
 
| 66 | W | March 14, 1959 | 5–0 | New York Rangers (1958–59) | 23–32–11 | 
 
| 67 | W | March 15, 1959 | 6–5 | @ New York Rangers (1958–59) | 24–32–11 | 
 
| 68 | W | March 19, 1959 | 6–3 | @ Montreal Canadiens (1958–59) | 25–32–11 | 
 
| 69 | W | March 21, 1959 | 5–1 | Chicago Black Hawks (1958–59) | 26–32–11 | 
 
| 70 | W | March 22, 1959 | 6–4 | @ Detroit Red Wings (1958–59) | 27–32–11 |