| Year | Winning team | Coach | Games | Losing team | Coach | Winning goal |
| 1927 | Ottawa Senators (C) (5, 4–1) | Dave Gill | 2–0 | Boston Bruins (A) (1, 0–1) | Art Ross | Cy Denneny (7:30, second) |
| 1928 | New York Rangers (A) (1, 1–0) | Lester Patrick-playing | 3–2 | Montreal Maroons (C) (2, 1–1) | Eddie Gerard | Frank Boucher (3:35, third) |
| 1929 | Boston Bruins (A) (2, 1–1) | Art Ross | 2–0 | New York Rangers (A) (2, 1–1) | Lester Patrick | Bill Carson (18:02, third) |
| 1930 | Montreal Canadiens (C) (6, 3–2) | Cecil Hart | 2–0 | Boston Bruins (A) (3, 1–2) | Art Ross | Howie Morenz (1:00, second) |
| 1931 | Montreal Canadiens (C) (7, 4–2) | 3–2 | Chicago Black Hawks (A) (1, 0–1) | Dick Irvin | Johnny Gagnon (9:59, second) |
| 1932 | Toronto Maple Leafs (C) (3, 3–0) | Dick Irvin | 3–0 | New York Rangers (A) (3, 1–2) | Lester Patrick | Ace Bailey (15:07, third) |
| 1933 | New York Rangers (A) (4, 2–2) | Lester Patrick | 3–1 | Toronto Maple Leafs (C) (4, 3–1) | Dick Irvin | Bill Cook (7:34, OT) |
| 1934 | Chicago Black Hawks (A) (2, 1–1) | Tommy Gorman | 3–1 | Detroit Red Wings (A) (1, 0–1) | Jack Adams | Mush March (10:05, second OT) |
| 1935 | Montreal Maroons (C) (3, 2–1) | 3–0 | Toronto Maple Leafs (C) (5, 3–2) | Dick Irvin | Baldy Northcott (16:18, second) |
| 1936 | Detroit Red Wings (A) (2, 1–1) | Jack Adams | 3–1 | Toronto Maple Leafs (C) (6, 3–3) | Pete Kelly (9:45, third) |
| 1937 | Detroit Red Wings (A) (3, 2–1) | 3–2 | New York Rangers (A) (5, 2–3) | Lester Patrick | Marty Barry (19:22, first) |
| 1938 | Chicago Black Hawks (A) (3, 2–1) | Bill Stewart | 3–1 | Toronto Maple Leafs (C) (7, 3–4) | Dick Irvin | Carl Voss (16:45, second) |
| 1939 | Boston Bruins (4, 2–2) | Art Ross | 4–1 | Toronto Maple Leafs (8, 3–5) | Roy Conacher (17:54, second) |
| 1940 | New York Rangers (6, 3–3) | Frank Boucher | 4–2 | Toronto Maple Leafs (9, 3–6) | Bryan Hextall (2:07, OT) |
| 1941 | Boston Bruins (5, 3–2) | Cooney Weiland | 4–0 | Detroit Red Wings (4, 2–2) | Jack Adams | Bobby Bauer (8:43, second) |
| 1942 | Toronto Maple Leafs (10, 4–6) | Hap Day | 4–3 | Detroit Red Wings (5, 2–3) | Jack Adams | Pete Langelle (9:48, third) |
| 1943 | Detroit Red Wings (6, 3–3) | Jack Adams | 4–0 | Boston Bruins (6, 3–3) | Art Ross | Joe Carveth (12:09, first) |
| 1944 | Montreal Canadiens (8, 5–2) | Dick Irvin | 4–0 | Chicago Black Hawks (4, 2–2) | Paul Thompson | Toe Blake (9:12, OT) |
| 1945 | Toronto Maple Leafs (11, 5–6) | Hap Day | 4–3 | Detroit Red Wings (7, 3–4) | Jack Adams | Babe Pratt (12:14, third) |
| 1946 | Montreal Canadiens (9, 6–2) | Dick Irvin | 4–1 | Boston Bruins (7, 3–4) | Dit Clapper | Toe Blake (11:06, third) |
| 1947 | Toronto Maple Leafs (12, 6–6) | Hap Day | 4–2 | Montreal Canadiens (10, 6–3) | Dick Irvin | Ted Kennedy (14:39, third) |
| 1948 | Toronto Maple Leafs (13, 7–6) | 4–0 | Detroit Red Wings (8, 3–5) | Tommy Ivan | Harry Watson (11:13, first) |
| 1949 | Toronto Maple Leafs (14, 8–6) | 4–0 | Detroit Red Wings (9, 3–6) | Cal Gardner (19:45, second) |
| 1950 | Detroit Red Wings (10, 4–6) | Tommy Ivan | 4–3 | New York Rangers (7, 3–4) | Lynn Patrick | Pete Babando (8:31, second OT) |
| 1951 | Toronto Maple Leafs (15, 9–6) | Joe Primeau | 4–1 | Montreal Canadiens (11, 6–4) | Dick Irvin | Bill Barilko (2:53, OT) |
| 1952 | Detroit Red Wings (11, 5–6) | Tommy Ivan | 4–0 | Montreal Canadiens (12, 6–5) | Metro Prystai (6:50, first) |
| 1953 | Montreal Canadiens (13, 7–5) | Dick Irvin | 4–1 | Boston Bruins (8, 3–5) | Lynn Patrick | Elmer Lach (1:22, OT) |
| 1954 | Detroit Red Wings (12, 6–6) | Tommy Ivan | 4–3 | Montreal Canadiens (14, 7–6) | Dick Irvin | Tony Leswick (4:20, OT) |
| 1955 | Detroit Red Wings (13, 7–6) | Jimmy Skinner | 4–3 | Montreal Canadiens (15, 7–7) | Gordie Howe (19:49, second) |
| 1956 | Montreal Canadiens (16, 8–7) | Toe Blake | 4–1 | Detroit Red Wings (14, 7–7) | Jimmy Skinner | Maurice Richard (15:08, second) |
| 1957 | Montreal Canadiens (17, 9–7) | 4–1 | Boston Bruins (9, 3–6) | Milt Schmidt | Dickie Moore (0:14, second) |
| 1958 | Montreal Canadiens (18, 10–7) | 4–2 | Boston Bruins (10, 3–7) | Bernie Geoffrion (19:26, second) |
| 1959 | Montreal Canadiens (19, 11–7) | 4–1 | Toronto Maple Leafs (16, 9–7) | Punch Imlach | Marcel Bonin (9:55, second) |
| 1960 | Montreal Canadiens (20, 12–7) | 4–0 | Toronto Maple Leafs (17, 9–8) | Jean Beliveau (8:16, first) |
| 1961 | Chicago Black Hawks (5, 3–2) | Rudy Pilous | 4–2 | Detroit Red Wings (15, 7–8) | Sid Abel | Ab McDonald (18:49, second) |
| 1962 | Toronto Maple Leafs (18, 10–8) | Punch Imlach | 4–2 | Chicago Black Hawks (6, 3–3) | Rudy Pilous | Dick Duff (14:14, third) |
| 1963 | Toronto Maple Leafs (19, 11–8) | 4–1 | Detroit Red Wings (16, 7–9) | Sid Abel | Eddie Shack (13:28, third) |
| 1964 | Toronto Maple Leafs (20, 12–8) | 4–3 | Detroit Red Wings (17, 7–10) | Andy Bathgate (3:04, first) |
| 1965 | Montreal Canadiens (21, 13–7) | Toe Blake | 4–3 | Chicago Black Hawks (7, 3–4) | Billy Reay | Jean Beliveau (0:14, first) |
| 1966 | Montreal Canadiens (22, 14–7) | 4–2 | Detroit Red Wings (18, 7–11) | Sid Abel | Henri Richard (2:20, OT) |
| 1967 | Toronto Maple Leafs (21, 13–8) | Punch Imlach | 4–2 | Montreal Canadiens (23, 14–8) | Toe Blake | Jim Pappin (19:24, second) |
| 1968 | Montreal Canadiens (E) (24, 15–8) | Toe Blake | 4–0 | St. Louis Blues (W) (1, 0–1) | Scotty Bowman | J. C. Tremblay (11:40, third) |
| 1969 | Montreal Canadiens (E) (25, 16–8) | Claude Ruel | 4–0 | St. Louis Blues (W) (2, 0–2) | John Ferguson (3:02, third) |
| 1970 | Boston Bruins (E) (11, 4–7) | Harry Sinden | 4–0 | St. Louis Blues (W) (3, 0–3) | Bobby Orr (0:40, OT) |
| 1971 | Montreal Canadiens (E) (26, 17–8) | Al MacNeil | 4–3 | Chicago Black Hawks (W) (8, 3–5) | Billy Reay | Henri Richard (2:34, third) |
| 1972 | Boston Bruins (E) (12, 5–7) | Tom Johnson | 4–2 | New York Rangers (E) (8, 3–5) | Emile Francis | Bobby Orr (11:18, first) |
| 1973 | Montreal Canadiens (E) (27, 18–8) | Scotty Bowman | 4–2 | Chicago Black Hawks (W) (9, 3–6) | Billy Reay | Yvan Cournoyer (8:13, third) |
| 1974 | Philadelphia Flyers (W) (1, 1–0) | Fred Shero | 4–2 | Boston Bruins (E) (13, 5–8) | Bep Guidolin | Rick MacLeish (14:48, first) |
| 1975 | Philadelphia Flyers (CC) (2, 2–0) | 4–2 | Buffalo Sabres (PW) (1, 0–1) | Floyd Smith | Bob Kelly (0:11, third) |