| Year | Year2 | Years | Name | Wins | Losses | Win % | Champs | Playoffs | Tenure | Notes |
|---|---|---|---|---|---|---|---|---|---|---|
| 2000 | 2018 | 2000-2018 | Larry Dolan | 1546 | 1475 | .512 | 3 | 19 | ||
| 1986 | 1999 | 1986-1999 | Richard E. Jacobs | 1119 | 1080 | .509 | 0 | 5 | 14 | |
| 1984 | 1985 | 1984-1985 | Estate of Steve O'Neill | 135 | 189 | .417 | 0 | 2 | ||
| 1979 | 1983 | 1979-1983 | Francis J. "Steve"" O'Neill" | 360 | 388 | .481 | 0 | 5 | ||
| 1977 | 1978 | 1977-1978 | Alva "Ted"" Bonda" | 140 | 180 | .437 | 0 | 2 | ||
| 1972 | 1976 | 1972-1976 | Nick Mileti | 380 | 418 | .476 | 0 | 5 | ||
| 1967 | 1971 | 1967-1971 | Vernon Stouffer | 359 | 449 | .444 | 0 | 5 | ||
| 1963 | 1966 | 1963-1966 | Gabe Paul | 326 | 322 | .503 | 0 | 4 | ||
| 1956 | 1962 | 1956-1962 | William R. Daley | 564 | 527 | .517 | 0 | 7 | ||
| 1953 | 1955 | 1953-1955 | Myron H. Wilson | 296 | 166 | .641 | 0 | 1 | 3 | |
| 1950 | 1952 | 1950-1952 | Ellis Ryan | 278 | 184 | .602 | 0 | 3 | ||
| 1947 | 1949 | 1947-1949 | Bill Veeck | 266 | 197 | .575 | 1 | 1 | 3 | |
| 1946 | 1946 | 1946 | Alva Bradley Bill Veeck | 68 | 86 | .442 | 0 | 1 | ||
| 1928 | 1945 | 1928-1945 | Alva Bradley | 1433 | 1319 | .521 | 0 | 18 | ||
| 1923 | 1927 | 1923-1927 | Estate of Jim Dunn | 373 | 394 | .486 | 0 | 5 | ||
| 1916 | 1922 | 1916-1922 | Jim Dunn | 592 | 444 | .571 | 1 | 1 | 7 | |
| 1901 | 1915 | 1901-1915 | Charles W. Somers | 1117 | 1127 | .498 | 0 | 15 | ||
