| No. |
R |
Date |
Score |
Opponent |
Record |
| 1 | L | October 11, 1968 | 2–4 | @ Boston Bruins (1968–69) | 0–1–0 |
| 2 | L | October 13, 1968 | 1–2 | Toronto Maple Leafs (1968–69) | 0–2–0 |
| 3 | W | October 17, 1968 | 7–2 | New York Rangers (1968–69) | 1–2–0 |
| 4 | L | October 20, 1968 | 2–4 | Montreal Canadiens (1968–69) | 1–3–0 |
| 5 | W | October 27, 1968 | 4–3 | Chicago Black Hawks (1968–69) | 2–3–0 |
| 6 | W | October 31, 1968 | 7–5 | Boston Bruins (1968–69) | 3–3–0 |
| 7 | L | November 2, 1968 | 1–2 | @ Montreal Canadiens (1968–69) | 3–4–0 |
| 8 | T | November 3, 1968 | 4–4 | St. Louis Blues (1968–69) | 3–4–1 |
| 9 | W | November 6, 1968 | 6–5 | @ Chicago Black Hawks (1968–69) | 4–4–1 |
| 10 | W | November 7, 1968 | 5–2 | Minnesota North Stars (1968–69) | 5–4–1 |
| 11 | L | November 9, 1968 | 4–6 | @ Minnesota North Stars (1968–69) | 5–5–1 |
| 12 | T | November 10, 1968 | 4–4 | Montreal Canadiens (1968–69) | 5–5–2 |
| 13 | L | November 13, 1968 | 1–2 | @ Oakland Seals (1968–69) | 5–6–2 |
| 14 | W | November 14, 1968 | 5–2 | @ Los Angeles Kings (1968–69) | 6–6–2 |
| 15 | T | November 16, 1968 | 1–1 | @ St. Louis Blues (1968–69) | 6–6–3 |
| 16 | L | November 20, 1968 | 2–3 | @ Montreal Canadiens (1968–69) | 6–7–3 |
| 17 | W | November 23, 1968 | 5–2 | @ Toronto Maple Leafs (1968–69) | 7–7–3 |
| 18 | W | November 27, 1968 | 5–2 | @ Philadelphia Flyers (1968–69) | 8–7–3 |
| 19 | L | November 28, 1968 | 1–3 | St. Louis Blues (1968–69) | 8–8–3 |
| 20 | T | December 1, 1968 | 3–3 | Philadelphia Flyers (1968–69) | 8–8–4 |
| 21 | W | December 4, 1968 | 7–2 | @ Pittsburgh Penguins (1968–69) | 9–8–4 |
| 22 | W | December 5, 1968 | 4–2 | New York Rangers (1968–69) | 10–8–4 |
| 23 | L | December 7, 1968 | 1–4 | @ Boston Bruins (1968–69) | 10–9–4 |
| 24 | W | December 8, 1968 | 5–2 | @ New York Rangers (1968–69) | 11–9–4 |
| 25 | L | December 11, 1968 | 3–6 | @ Los Angeles Kings (1968–69) | 11–10–4 |
| 26 | L | December 12, 1968 | 0–6 | @ Oakland Seals (1968–69) | 11–11–4 |
| 27 | W | December 14, 1968 | 3–1 | Oakland Seals (1968–69) | 12–11–4 |
| 28 | W | December 15, 1968 | 5–2 | Minnesota North Stars (1968–69) | 13–11–4 |
| 29 | L | December 19, 1968 | 0–2 | Chicago Black Hawks (1968–69) | 13–12–4 |
| 30 | L | December 21, 1968 | 3–8 | @ Toronto Maple Leafs (1968–69) | 13–13–4 |
| 31 | W | December 22, 1968 | 3–2 | Toronto Maple Leafs (1968–69) | 14–13–4 |
| 32 | L | December 25, 1968 | 3–6 | @ Pittsburgh Penguins (1968–69) | 14–14–4 |
| 33 | T | December 27, 1968 | 3–3 | Philadelphia Flyers (1968–69) | 14–14–5 |
| 34 | T | December 29, 1968 | 3–3 | Boston Bruins (1968–69) | 14–14–6 |
| 35 | W | December 31, 1968 | 6–3 | Minnesota North Stars (1968–69) | 15–14–6 |
| 36 | L | January 1, 1969 | 1–4 | @ Chicago Black Hawks (1968–69) | 15–15–6 |
| 37 | L | January 4, 1969 | 1–3 | @ St. Louis Blues (1968–69) | 15–16–6 |
| 38 | W | January 5, 1969 | 2–1 | Pittsburgh Penguins (1968–69) | 16–16–6 |
| 39 | W | January 9, 1969 | 6–2 | Los Angeles Kings (1968–69) | 17–16–6 |
| 40 | W | January 11, 1969 | 3–2 | New York Rangers (1968–69) | 18–16–6 |
| 41 | W | January 12, 1969 | 5–1 | Oakland Seals (1968–69) | 19–16–6 |
| 42 | W | January 15, 1969 | 4–0 | @ Montreal Canadiens (1968–69) | 20–16–6 |
| 43 | W | January 16, 1969 | 3–2 | Pittsburgh Penguins (1968–69) | 21–16–6 |
| 44 | T | January 18, 1969 | 1–1 | @ Toronto Maple Leafs (1968–69) | 21–16–7 |
| 45 | L | January 19, 1969 | 1–3 | @ Philadelphia Flyers (1968–69) | 21–17–7 |
| 46 | T | January 23, 1969 | 2–2 | Boston Bruins (1968–69) | 21–17–8 |
| 47 | W | January 25, 1969 | 5–3 | Oakland Seals (1968–69) | 22–17–8 |
| 48 | W | January 26, 1969 | 3–2 | Toronto Maple Leafs (1968–69) | 23–17–8 |
| 49 | L | January 29, 1969 | 0–2 | @ New York Rangers (1968–69) | 23–18–8 |
| 50 | L | February 1, 1969 | 0–2 | St. Louis Blues (1968–69) | 23–19–8 |
| 51 | L | February 2, 1969 | 2–4 | @ Boston Bruins (1968–69) | 23–20–8 |
| 52 | W | February 4, 1969 | 2–0 | @ Philadelphia Flyers (1968–69) | 24–20–8 |
| 53 | W | February 6, 1969 | 6–1 | Chicago Black Hawks (1968–69) | 25–20–8 |
| 54 | W | February 8, 1969 | 3–1 | @ Chicago Black Hawks (1968–69) | 26–20–8 |
| 55 | W | February 9, 1969 | 5–0 | Los Angeles Kings (1968–69) | 27–20–8 |
| 56 | L | February 13, 1969 | 1–3 | Montreal Canadiens (1968–69) | 27–21–8 |
| 57 | L | February 15, 1969 | 2–6 | @ Minnesota North Stars (1968–69) | 27–22–8 |
| 58 | W | February 16, 1969 | 6–3 | Los Angeles Kings (1968–69) | 28–22–8 |
| 59 | T | February 19, 1969 | 1–1 | @ New York Rangers (1968–69) | 28–22–9 |
| 60 | W | February 20, 1969 | 3–0 | Pittsburgh Penguins (1968–69) | 29–22–9 |
| 61 | L | February 22, 1969 | 2–3 | @ Pittsburgh Penguins (1968–69) | 29–23–9 |
| 62 | W | February 23, 1969 | 9–1 | Philadelphia Flyers (1968–69) | 30–23–9 |
| 63 | L | February 26, 1969 | 2–7 | @ Montreal Canadiens (1968–69) | 30–24–9 |
| 64 | W | March 1, 1969 | 4–2 | @ Minnesota North Stars (1968–69) | 31–24–9 |
| 65 | W | March 2, 1969 | 4–2 | Montreal Canadiens (1968–69) | 32–24–9 |
| 66 | T | March 5, 1969 | 2–2 | @ Boston Bruins (1968–69) | 32–24–10 |
| 67 | L | March 6, 1969 | 1–4 | New York Rangers (1968–69) | 32–25–10 |
| 68 | W | March 8, 1969 | 7–4 | Boston Bruins (1968–69) | 33–25–10 |
| 69 | L | March 15, 1969 | 2–3 | @ St. Louis Blues (1968–69) | 33–26–10 |
| 70 | L | March 16, 1969 | 4–6 | @ New York Rangers (1968–69) | 33–27–10 |
| 71 | T | March 19, 1969 | 4–4 | @ Oakland Seals (1968–69) | 33–27–11 |
| 72 | L | March 20, 1969 | 2–4 | @ Los Angeles Kings (1968–69) | 33–28–11 |
| 73 | L | March 22, 1969 | 1–3 | @ Toronto Maple Leafs (1968–69) | 33–29–11 |
| 74 | L | March 27, 1969 | 2–4 | Toronto Maple Leafs (1968–69) | 33–30–11 |
| 75 | T | March 29, 1969 | 1–1 | Chicago Black Hawks (1968–69) | 33–30–12 |
| 76 | L | March 30, 1969 | 5–9 | @ Chicago Black Hawks (1968–69) | 33–31–12 |