| Year | Year2 | Years | Name | Wins | Losses | Win % | Champs | Playoffs | Tenure | Notes |
|---|---|---|---|---|---|---|---|---|---|---|
| 1998 | 2018 | 1998-2018 | Brian Cashman | 1963 | 1380 | .587 | 4 | 14 | 21 | |
| 1996 | 1997 | 1996-1997 | Bob Watson | 188 | 136 | .580 | 1 | 2 | 2 | |
| 1980 | 1995 | 1980-1995 | Gene Michael | 546 | 466 | .540 | 0 | 3 | 7 | |
| 1990 | 1990 | 1990 | Harding Peterson | 67 | 95 | .414 | 0 | 1 | ||
| 1989 | 1989 | 1989 | Bob Quinn | 74 | 87 | .460 | 0 | 1 | ||
| 1988 | 1988 | 1988 | Bob Quinn Lou Piniella | 85 | 76 | .528 | 0 | 1 | ||
| 1987 | 1987 | 1987 | Woody Woodward | 89 | 73 | .549 | 0 | 1 | ||
| 1985 | 1986 | 1985-1986 | Clyde King | 187 | 136 | .579 | 0 | 2 | ||
| 1984 | 1984 | 1984 | Murray Cook | 87 | 75 | .537 | 0 | 1 | ||
| 1982 | 1983 | 1982-1983 | Bill Bergesch | 170 | 154 | .525 | 0 | 2 | ||
| 1978 | 1979 | 1978-1979 | Cedric Tallis | 189 | 134 | .585 | 1 | 1 | 2 | |
| 1976 | 1977 | 1976-1977 | Gabe Paul | 197 | 124 | .614 | 1 | 2 | 2 | |
| 1974 | 1975 | 1974-1975 | Gabe Paul Tal Smith | 172 | 150 | .534 | 0 | 2 | ||
| 1967 | 1973 | 1967-1973 | Lee MacPhail | 569 | 557 | .505 | 0 | 7 | ||
| 1966 | 1966 | 1966 | Dan Topping | 70 | 89 | .440 | 0 | 1 | ||
| 1964 | 1965 | 1964-1965 | Ralph Houk | 176 | 148 | .543 | 0 | 1 | 2 | |
| 1962 | 1963 | 1962-1963 | Roy Hamey | 200 | 123 | .619 | 1 | 2 | 2 | |
| 1947 | 1961 | 1947-1961 | George Weiss | 1449 | 866 | .626 | 9 | 12 | 15 | |
| 1945 | 1946 | 1945-1946 | Larry MacPhail | 168 | 138 | .549 | 0 | 2 | ||
| 1920 | 1944 | 1920-1944 | Ed Barrow | 2376 | 1453 | .621 | 10 | 14 | 25 | |
