| # | Manager | Seasons | W | L | T | Pct | Post | Titles | |
|---|---|---|---|---|---|---|---|---|---|
| 1 | George Stallings | 1897–1898 | 75 | 103 | 2 | .422 | — | ||
| 2 | Bill Shettsline | 1898–1902 | 366 | 304 | 7 | .546 | — | ||
| 3 | Chief Zimmer | 1903 | 49 | 86 | 4 | .367 | — | ||
| 4 | Hugh Duffy | 1904–1906 | 206 | 251 | 7 | .452 | — | ||
| 5 | Billy Murray | 1907–1909 | 240 | 213 | 5 | .529 | — | ||
| 6 | Red Dooin | 1910–1914 | 392 | 370 | 13 | .514 | — | ||
| 7 | Pat Moran | 1915–1918 | 323 | 257 | 6 | .556 | 1–4 | ||
| 8 | Jack Coombs | 1919 | 18 | 44 | 1 | .294 | — | ||
| 9 | Gavvy Cravath | 1919–1920 | 91 | 137 | 0 | .399 | — | ||
| 10 | Bill Donovan | 1921 | 25 | 62 | 0 | .287 | — | ||
| 11 | Kaiser Wilhelm | 1921–1922 | 83 | 137 | 1 | .378 | — | ||
| 12 | Art Fletcher | 1923–1926 | 231 | 378 | 3 | .380 | — | ||
| 13 | Stuffy McInnis | 1927 | 51 | 103 | 1 | .332 | — | ||
| 14 | Burt Shotton | 1928–1933 | 370 | 549 | 4 | .403 | — | ||
| 15 | Jimmie Wilson | 1934–1938 | 280 | 477 | 6 | .371 | — | ||
| 16 | Hans Lobert | 1938–1942 | 42 | 111 | 0 | .275 | — | ||
| 17 | Doc Prothro | 1939–1941 | 138 | 320 | 2 | .302 | — | ||
| 19 | Freddie Fitzsimmons | 1943–1945 | 104 | 180 | 2 | .367 | — | ||
| 18 | Bucky Harris | 1943 | 39 | 53 | 2 | .426 | — | ||
| 20 | Ben Chapman | 1945–1948 | 196 | 276 | 2 | .416 | — | ||
| 21 | Eddie Sawyer | 1948–1960 | 389 | 422 | 4 | .480 | 0–4 | ||
| 22 | Steve O'Neill | 1952–1954 | 182 | 140 | 2 | .565 | — | ||
| 23 | Mayo Smith | 1955–1958 | 265 | 283 | 2 | .484 | — | ||
| 24 | Gene Mauch | 1960–1968 | 645 | 684 | 2 | .485 | — | ||
| 25 | Bob Skinner | 1968–1969 | 92 | 123 | 0 | .428 | — | ||
| 26 | Frank Lucchesi | 1970–1972 | 166 | 233 | 0 | .416 | — | ||
| 27 | Paul Owens | 1972–1984 | 161 | 158 | 0 | .505 | 4–5 | ||
| 28 | Danny Ozark | 1973–1979 | 594 | 510 | 1 | .538 | 2–9 | ||
| 29 | Dallas Green | 1979–1981 | 169 | 130 | 0 | .565 | 9–7 | 1980 | |
| 30 | Pat Corrales | 1982–1983 | 132 | 115 | 1 | .534 | — | ||
| 31 | John Felske | 1985–1987 | 190 | 194 | 0 | .495 | — | ||
| 32 | Lee Elia | 1987–1988 | 111 | 142 | 1 | .439 | — | ||
| 33 | Nick Leyva | 1989–1991 | 148 | 189 | 1 | .439 | — | ||
| 34 | Jim Fregosi | 1991–1996 | 431 | 463 | 0 | .482 | 6–6 | ||
| 35 | Terry Francona | 1997–2000 | 285 | 363 | 0 | .440 | — | ||
| 36 | Larry Bowa | 2001–2004 | 337 | 308 | 0 | .522 | — | ||
| 37 | Charlie Manuel | 2005–2013 | 780 | 636 | 0 | .551 | 27–19 | 2008 | |
| 38 | Ryne Sandberg | 2013–2015 | 119 | 159 | 0 | .428 | — | ||
| 39 | Pete Mackanin | 2015–2017 | 174 | 238 | 0 | .422 | — | ||
| 40 | Gabe Kapler | 2018–2019 | 161 | 163 | 0 | .497 | — | ||
| 41 | Joe Girardi | 2020–2022 | 132 | 141 | 0 | .484 | — | ||
| 42 | Rob Thomson | 2022–2025 | 346 | 251 | 0 | .580 | 21–17 |
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