| Season | Manager | Order | G | W | L | PCT. | Notes |
|---|---|---|---|---|---|---|---|
| 1887 | William Bryan | Split | |||||
| 1887 | Chrlie Morton | Split | |||||
| 1888 | Charlie Morton | 1 of 1 | 113 | 73 | 40 | 0.64601769911504 | |
| 1889 | James Macullar | 1 of 1 | 128 | 41 | 77 | 0.3203125 | |
| 1890 | James Macullar | 1 of 1 | 121 | 48 | 73 | 0.39669421487603 | |
| 1894 | Hugh Nicol | Split | |||||
| 1894 | Bill Traffley | Split | |||||
| 1895 | Bill Traffley | 1 of 1 | 126 | 71 | 55 | 0.56349206349206 | |
| 1896 | Bill Traffley | 1 of 1 | 78 | 56 | 22 | 0.71794871794872 | |
| 1897 | George “Pete” Lohman | 1 of 1 | 124 | 67 | 57 | 0.54032258064516 | |
| 1900 | Belden Hill | 1 of 1 | 104 | 59 | 45 | 0.56730769230769 | |
| 1901 | Mike Kelly | Splits? | |||||
| 1902 | Joe Quinn | 1 of 1 | 137 | 54 | 83 | 0.39416058394161 | |
| 1903 | Joe Quinn | 1 of 1 | 131 | 55 | 76 | 0.41984732824427 | |
| 1904 | Bill Hofer | Split | |||||
| 1904 | Joe Quinn | Split | |||||
| 1905 | Herman Long | 1 of 1 | 149 | 95 | 54 | 0.63758389261745 | |
| 1906 | Jack Doyle | 1 of 1 | 147 | 97 | 50 | 0.65986394557823 | |
| 1907 | Mike Kelley | 1 of 1 | 139 | 76 | 63 | 0.54676258992806 | |
| 1908 | Charles Dexter | 1 of 1 | 148 | 54 | 94 | 0.36486486486486 | |
| 1909 | Bill Dwyer | 1 of 1 | 152 | 93 | 59 | 0.61184210526316 | Bill vs George? |
| 1910 | George Dwyer | 1 of 1 | 168 | 72 | 96 | 0.42857142857143 | George vs Bill? |
| 1911 | George Dwyer | Split | |||||
| 1911 | George Davis | Split | |||||
| 1912 | Frank Isbell | 1 of 1 | 162 | 82 | 80 | 0.50617283950617 | |
| 1913 | Frank Isbell | 1 of 1 | 165 | 93 | 72 | 0.56363636363636 | |
| 1914 | Frank Isbell | 1 of 1 | 163 | 82 | 81 | 0.50306748466258 | |
| 1915 | Frank Isbell | 1 of 1 | 140 | 87 | 53 | 0.62142857142857 | |
| 1916 | Frank Isbell | 1 of 1 | 150 | 75 | 75 | 0.5 | |
| 1917 | Jack Coffey | 1 of 1 | 146 | 84 | 62 | 0.57534246575342 | |
| 1918 | Jack Coffey | 1 of 1 | 65 | 34 | 31 | 0.52307692307692 | World War I |
| 1919 | Jack Coffey | 1 of 1 | 138 | 71 | 67 | 0.51449275362319 | |
| 1920 | Jack Coffey | 1 of 1 | 151 | 58 | 93 | 0.3841059602649 | |
| 1921 | Jack Coffey | 1 of 1 | 163 | 71 | 92 | 0.43558282208589 | |
| 1922 | Dick Breen | Split | |||||
| 1922 | Jack Graney | Split | |||||
| 1923 | |||||||
| 1924 | |||||||
| 1925 | |||||||
| 1926 | |||||||
| 1927 | |||||||
| 1928 | |||||||
| 1929 | |||||||
| 1930 | |||||||
| 1931 | |||||||
| 1932 | |||||||
| 1933 | |||||||
| 1934 | |||||||
| 1935 | |||||||
| 1936 | |||||||
| 1937 | |||||||
| 1947 | |||||||
| 1948 | |||||||
| 1949 | |||||||
| 1950 | |||||||
| 1951 | |||||||
| 1952 | |||||||
| 1953 | |||||||
| 1954 | |||||||
| 1955 | |||||||
| 1956 | Lou Klein | 1 of 1 | 137 | 72 | 65 | 0.52554744525547 | |
| 1957 | Lou Stringer | 1 of 2 | Needs split | ||||
| 1957 | Hershel Martin | 2 of 2 | Needs split | ||||
| 1958 | Roy Hartsfield | 1 of 1 | 144 | 61 | 83 | 0.42361111111111 | |
| 1959 | Chuck Kress | 1 of 1 | 127 | 78 | 48 | 0.61417322834646 | |
| 1960 | Andy Seminick | 1 of 1 | 138 | 64 | 74 | 0.46376811594203 | |
| 1961 | Charlie Kress | 1 of 1 | 130 | 37 | 93 | 0.28461538461538 | |
| 1969 | Jimmy Williams | 1 of 1 | 140 | 62 | 78 | 0.44285714285714 | |
| 1970 | Sherm Lollar | 1 of 1 | 139 | 70 | 68 | 0.50359712230216 | |
| 1971 | Sherm Lollar | 1 of 1 | 140 | 71 | 69 | 0.50714285714286 | |
| 1972 | Sherm Lollar | 1 of 1 | 140 | 62 | 78 | 0.44285714285714 | |
| 1973 | Joe Sparks | 1 of 1 | 137 | 83 | 53 | 0.60583941605839 | |
| 1974 | Joe Sparks | 1 of 1 | 136 | 74 | 62 | 0.54411764705882 | |
| 1975 | Joe Sparks | 1 of 1 | 135 | 56 | 79 | 0.41481481481481 | |
| 1976 | Loren Babe | 1 of 1 | 137 | 68 | 68 | 0.4963503649635 | |
| 1977 | Joe Sparks | 1 of 1 | 136 | 61 | 75 | 0.44852941176471 | |
| 1978 | Joe Sparks | 1 of 1 | 136 | 66 | 70 | 0.48529411764706 | |
| 1979 | Joe Sparks | 2 of 2 | Need split with LaRussa | ||||
| 1979 | Tony La Russa | 1 of 2 | Need split with Sparks | ||||
| 1980 | Pete Ward | 1 of 1 | 136 | 59 | 77 | 0.43382352941176 | |
| 1981 | Roy Hartsfield | 1 of 2 | Confirm order | ||||
| 1981 | Randy Hundley | 2 of 2 | Confirm order | ||||
| 1982 | Jim Napier | 1 of 1 | 135 | 73 | 62 | 0.54074074074074 | |
| 1983 | Jim Napier | 1 of 1 | 136 | 70 | 66 | 0.51470588235294 | |
| 1984 | Jim Napier | 1 of 1 | 154 | 80 | 74 | 0.51948051948052 | |
| 1985 | Larry Cox | 1 of 1 | 141 | 66 | 75 | 0.46808510638298 | |
| 1986 | Larry Cox | 1 of 1 | 142 | 74 | 68 | 0.52112676056338 | |
| 1987 | Larry Cox | 1 of 1 | 138 | 64 | 74 | 0.46376811594203 | |
| 1988 | Pete Mackanin | 1 of 2 | Confirm order *were there 2 managers? | ||||
| 1988 | Larry Cox | 2 of 2 | Confirm order | ||||
| 1989 | Pete Mackanin | 1 of 1 | 144 | 62 | 82 | 0.43055555555556 | |
| 1990 | Jim Essian | 1 of 1 | 146 | 72 | 74 | 0.49315068493151 | |
| 1991 | Jim Essian | 1 of 2 | 37 | 22 | 15 | 0.59459459459459 | Confirm order |
| 1991 | Mick Kelleher | 2 of 2 | 107 | 56 | 51 | 0.52336448598131 | Confirm order |
| 1992 | Brad Mills | 1 of 1 | 143 | 51 | 92 | 0.35664335664336 | |
| 1993 | Marv Foley | 1 of 1 | 144 | 85 | 59 | 0.59027777777778 | |
| 1994 | Rick Patterson | 1 of 1 | 143 | 69 | 74 | 0.48251748251748 | |
| 1995 | Ron Clark | 1 of 1 | 143 | 69 | 74 | 0.48251748251748 | |
| 1996 | Ron Clark | 1 of 1 | 142 | 64 | 78 | 0.45070422535211 | |
| 1997 | Tim Johnson | 1 of 1 | 143 | 74 | 69 | 0.51748251748252 | |
| 1998 | Terry Kennedy | 1 of 1 | 144 | 85 | 59 | 0.59027777777778 | |
| 1999 | Terry Kennedy | 1 of 1 | 141 | 65 | 76 | 0.46099290780142 | |
| 2000 | Dave Trembley | 1 of 1 | 144 | 57 | 87 | 0.39583333333333 | |
| 2001 | Bruce Kimm | 1 of 1 | 143 | 83 | 60 | 0.58041958041958 | |
| 2002 | Pat Listach | 2 of 2 | 55 | 27 | 28 | 0.49090909090909 | Replaced B. Kimm on 7/05 |
| 2002 | Bruce Kimm | 1 of 2 | 89 | 44 | 45 | 0.49438202247191 | Replaced by Pat Listach on 07/05 |
| 2003 | Mike Quade | 1 of 1 | 142 | 70 | 72 | 0.49295774647887 | |
| 2004 | Mike Quade | 1 of 1 | 143 | 79 | 64 | 0.55244755244755 | |
| 2005 | Mike Quade | 1 of 1 | 139 | 64 | 75 | 0.46043165467626 | |
| 2006 | Bobby Dickerson | 1 of 1 | 144 | 76 | 68 | 0.52777777777778 | |
| 2007 | Buddy Bailey | 1 of 1 | 144 | 79 | 65 | 0.54861111111111 | |
| 2008 | Pat Listach | 1 of 1 | 142 | 83 | 59 | 0.58450704225352 | |
| 2009 | Bobby Dickerson | 1 of 1 | 144 | 72 | 72 | 0.5 | |
| 2010 | Ryne Sandberg | 1 of 1 | 144 | 82 | 62 | 0.56944444444444 | |
| 2011 | Bill Dancy | 1 of 1 | 140 | 64 | 76 | 0.45714285714286 | |
| 2012 | Dave Bialas | 1 of 1 | 140 | 53 | 87 | 0.37857142857143 | |
| 2013 | Marty Pevey | 1 of 1 | 144 | 66 | 78 | 0.45833333333333 | |
| 2014 | Marty Pevey | 1 of 1 | 144 | 74 | 70 | 0.51388888888889 | |
| 2015 | Marty Pevey | 1 of 1 | 144 | 80 | 64 | 0.55555555555556 | |
| 2016 | Marty Pevey | 1 of 1 | 143 | 67 | 76 | 0.46853146853147 | |
| 2017 | Marty Pevey | 1 of 1 | 139 | 67 | 72 | 0.48201438848921 | |
| 2018 | Marty Pevey | 1 of 1 | 138 | 50 | 88 | 0.36231884057971 | |
| 2019 | Marty Pevey | 1 of 1 | 140 | 75 | 65 | 0.53571428571429 | |
| 2021 | Marty Pevey | 1 of 1 | 129 | 51 | 78 | 0.3953488372093 | |
| 2022 | Marty Pevey | 1 of 1 | 149 | 68 | 81 | 0.45637583892617 | |
| 2023 | Marty Pevey | 1 of 1 | 147 | 82 | 65 | 0.5578231292517 | |
| 2024 | Marty Pevey | 1 of 1 | 150 | 68 | 82 | 0.45333333333333 | |
| 2025 | Marty Pevey | 1 of 1 |
