| Year | Year2 | Years | Name | Wins | Losses | Win % | Champs | Playoffs | Tenure | Notes |
|---|---|---|---|---|---|---|---|---|---|---|
| 2012 | 2018 | 2012-2018 | Dan Duquette | 552 | 529 | .511 | 1 | 7 | ||
| 2008 | 2011 | 2008-2011 | Andy MacPhail | 267 | 380 | .413 | 0 | 4 | ||
| 2007 | 2007 | 2007 | Andy MacPhail Mike Flanagan | 69 | 93 | .426 | 0 | 1 | ||
| 2006 | 2006 | 2006 | Mike Flanagan | 70 | 92 | .432 | 0 | 1 | ||
| 2003 | 2005 | 2003-2005 | Jim Beattie Mike Flanagan | 223 | 263 | .459 | 0 | 3 | ||
| 2000 | 2002 | 2000-2002 | Syd Thrift | 204 | 281 | .421 | 0 | 3 | ||
| 1999 | 1999 | 1999 | Frank Wren | 78 | 84 | .481 | 0 | 1 | ||
| 1996 | 1998 | 1996-1998 | Pat Gillick | 265 | 221 | .545 | 2 | 3 | ||
| 1988 | 1995 | 1988-1995 | Roland Hemond | 592 | 634 | .483 | 0 | 8 | ||
| 1976 | 1987 | 1976-1987 | Hank Peters | 1036 | 845 | .551 | 1 | 2 | 12 | |
| 1972 | 1975 | 1972-1975 | Frank Cashen | 358 | 279 | .562 | 2 | 4 | ||
| 1966 | 1971 | 1966-1971 | Harry Dalton | 582 | 383 | .603 | 2 | 4 | 6 | |
| 1959 | 1965 | 1959-1965 | Lee MacPhail | 612 | 506 | .547 | 0 | 7 | ||
| 1955 | 1958 | 1955-1958 | Paul Richards | 276 | 337 | .450 | 0 | 4 | ||
| 1954 | 1954 | 1954 | Art Ehlers | 54 | 100 | .351 | 0 | 1 | ||
| 1952 | 1953 | 1952-1953 | Bill Veeck | 118 | 190 | .383 | 0 | 2 | ||
| 1937 | 1951 | 1937-1951 | Bill DeWitt | 952 | 1347 | .414 | 0 | 1 | 15 | |
