| # | Manager | Seasons | W | L | T | Pct | Post | Titles | |
|---|---|---|---|---|---|---|---|---|---|
| 38 | Stephen Vogt | 2024–2025 | 180 | 143 | 0 | .557 | 5–8 | ||
| 37.1 | DeMarlo Hale* | 2021 | 30 | 33 | 0 | .476 | — | ||
| 37 | Terry Francona | 2013–2023 | 891 | 724 | 0 | .552 | 16–17 | ||
| 36.1 | Sandy Alomar* | 2012 | 3 | 3 | 0 | .500 | — | ||
| 36 | Manny Acta | 2010–2012 | 214 | 266 | 0 | .446 | — | ||
| 35 | Eric Wedge | 2003–2009 | 561 | 573 | 0 | .495 | 6–5 | ||
| 34.1 | Joel Skinner* | 2002 | 35 | 41 | 0 | .461 | — | ||
| 34 | Charlie Manuel | 2000–2002 | 220 | 190 | 0 | .537 | 2–3 | ||
| 33 | Mike Hargrove | 1991–1999 | 721 | 591 | 0 | .550 | 27–25 | ||
| 32 | John McNamara | 1990–1991 | 102 | 137 | 0 | .427 | — | ||
| 31.1 | John Hart* | 1989 | 8 | 11 | 0 | .421 | — | ||
| 31 | Doc Edwards | 1987–1989 | 173 | 207 | 0 | .455 | — | ||
| 30 | Pat Corrales | 1983–1987 | 280 | 355 | 2 | .441 | — | ||
| 29 | Mike Ferraro | 1983 | 40 | 60 | 0 | .400 | — | ||
| 28 | Dave Garcia | 1979–1982 | 247 | 244 | 0 | .503 | — | ||
| 27 | Jeff Torborg | 1977–1979 | 157 | 201 | 0 | .439 | — | ||
| 26 | Frank Robinson | 1975–1977 | 186 | 189 | 0 | .496 | — | ||
| 25 | Ken Aspromonte | 1972–1974 | 220 | 259 | 1 | .459 | — | ||
| 24.1 | Johnny Lipon* | 1971 | 17 | 41 | 0 | .293 | — | ||
| 24 | Alvin Dark | 1968–1971 | 267 | 321 | 1 | .454 | — | ||
| 23 | Joe Adcock | 1967 | 75 | 87 | 0 | .463 | — | ||
| 22 | George Strickland | 1964–1966 | 48 | 63 | 1 | .433 | — | ||
| 21 | Birdie Tebbetts | 1963–1966 | 278 | 259 | 1 | .518 | — | ||
| 20 | Mel McGaha | 1962 | 78 | 82 | 0 | .487 | — | ||
| 19.1 | Mel Harder* | 1961–1962 | 3 | 0 | 0 | 1.000 | — | ||
| 19 | Jimmy Dykes | 1960–1961 | 103 | 115 | 0 | .472 | — | ||
| 18.1 | Jo-Jo White* | 1960 | 1 | 0 | 0 | 1.000 | — | ||
| 17 | Bobby Bragan | 1958 | 31 | 36 | 0 | .463 | — | ||
| 18 | Joe Gordon | 1958–1960 | 184 | 151 | 0 | .549 | — | ||
| 16 | Kerby Farrell | 1957 | 76 | 77 | 0 | .497 | — | ||
| 15 | Al Lopez | 1951–1956 | 570 | 354 | 6 | .616 | 0–4 | ||
| 14 | Lou Boudreau | 1942–1950 | 727 | 649 | 12 | .528 | 5–2 | 1948 | |
| 13 | Ossie Vitt | 1938–1940 | 262 | 198 | 2 | .569 | — | ||
| 12 | Steve O'Neill | 1935–1937 | 199 | 169 | 5 | .540 | — | ||
| 10.1 | Bibb Falk* | 1933 | 1 | 0 | 0 | 1.000 | — | ||
| 11 | Walter Johnson | 1933–1935 | 179 | 168 | 2 | .516 | — | ||
| 10 | Roger Peckinpaugh | 1928–1941 | 490 | 481 | 4 | .505 | — | ||
| 9 | Jack McCallister | 1927 | 66 | 87 | 0 | .431 | — | ||
| 8 | Tris Speaker | 1919–1926 | 617 | 520 | 2 | .543 | 5–2 | 1920 | |
| 7 | Lee Fohl | 1915–1919 | 327 | 309 | 10 | .514 | — | ||
| 6 | Joe Birmingham | 1912–1915 | 170 | 191 | 7 | .471 | — | ||
| 5 | Harry Davis | 1912 | 54 | 71 | 2 | .433 | — | ||
| 4.1 | George Stovall* | 1911 | 74 | 62 | 3 | .543 | — | ||
| 4 | Deacon McGuire | 1909–1911 | 91 | 117 | 11 | .441 | — | ||
| 3 | Nap Lajoie | 1905–1909 | 397 | 330 | 14 | .545 | — | ||
| 2 | Bill Armour | 1902–1904 | 232 | 195 | 4 | .543 | — | ||
| 1 | Jimmy McAleer | 1901 | 54 | 82 | 2 | .399 | — |
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