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| 2005 | Chicago Cubs | NL | Central | 79 | 83 | .488 | 21.0 | 4 | Dusty Baker | | |
| 2004 | Chicago Cubs | NL | Central | 89 | 73 | .549 | 16.0 | 3 | Dusty Baker | Wrigley Field | |
| 2003 | Chicago Cubs | NL | Central | 88 | 74 | .543 | - | 1 | Dusty Baker | Wrigley Field | Lost NLCS (Marlins) |
| 2002 | Chicago Cubs | NL | Central | 67 | 95 | .414 | 30.0 | 5 | Bruce Kimm, Don Baylor | Wrigley Field | |
| 2001 | Chicago Cubs | NL | Central | 88 | 74 | .543 | 5.0 | 3 | Don Baylor | Wrigley Field | |
| 2000 | Chicago Cubs | NL | Central | 65 | 97 | .401 | 30.0 | 6 | Don Baylor | Wrigley Field | |
| 1999 | Chicago Cubs | NL | Central | 67 | 95 | .414 | 30.0 | 6 | Jim Riggleman | Wrigley Field | |
| 1998 | Chicago Cubs | NL | Central | 90 | 73 | .552 | 12.5 | 2 | Jim Riggleman | Wrigley Field | Lost in 1st Round (Braves) |
| 1997 | Chicago Cubs | NL | Central | 68 | 94 | .420 | 16.0 | 5 | Jim Riggleman | Wrigley Field | |
| 1996 | Chicago Cubs | NL | Central | 76 | 86 | .469 | 12.0 | 4 | Jim Riggleman | Wrigley Field | |
| 1995 | Chicago Cubs | NL | Central | 73 | 71 | .507 | 12.0 | 3 | Jim Riggleman | Wrigley Field | |
| 1994 | Chicago Cubs | NL | Central | 49 | 64 | .434 | 16.5 | 5 | Tom Trebelhorn | Wrigley Field | |
| 1993 | Chicago Cubs | NL | East | 84 | 78 | .519 | 13.0 | 4 | Jim Lefebvre | Wrigley Field | |
| 1992 | Chicago Cubs | NL | East | 78 | 84 | .481 | 18.0 | 4 | Jim Lefebvre | Wrigley Field | |
| 1991 | Chicago Cubs | NL | East | 77 | 83 | .481 | 20.0 | 4 | Joe Altobelli, Don Zimmer, Jim Essian | Wrigley Field | |
| 1990 | Chicago Cubs | NL | East | 77 | 85 | .475 | 18.0 | 5 | Don Zimmer | Wrigley Field | |
| 1989 | Chicago Cubs | NL | East | 93 | 69 | .574 | - | 1 | Don Zimmer | Wrigley Field | Lost NLCS (Giants) |
| 1988 | Chicago Cubs | NL | East | 77 | 85 | .475 | 24.0 | 4 | Don Zimmer | Wrigley Field | |
| 1987 | Chicago Cubs | NL | East | 76 | 85 | .472 | 18.5 | 6 | Frank Lucchesi, Gene Michael | Wrigley Field | |
| 1986 | Chicago Cubs | NL | East | 70 | 90 | .438 | 37.0 | 5 | John Vukovich, Jim Frey, Gene Michael | Wrigley Field | |
| 1985 | Chicago Cubs | NL | East | 77 | 84 | .478 | 23.5 | 4 | Jim Frey | Wrigley Field | |
| 1984 | Chicago Cubs | NL | East | 96 | 65 | .596 | - | 1 | Jim Frey | Wrigley Field | Lost NLCS (Padres) |
| 1983 | Chicago Cubs | NL | East | 71 | 91 | .438 | 19.0 | 5 | Charlie Fox, Lee Elia | Wrigley Field | |
| 1982 | Chicago Cubs | NL | East | 73 | 89 | .451 | 19.0 | 5 | Lee Elia | Wrigley Field | |
| 1981 | Chicago Cubs | NL | East | 38 | 65 | .369 | | | Joey Amalfitano | Wrigley Field | |
| 1980 | Chicago Cubs | NL | East | 64 | 98 | .395 | 27.0 | 6 | Joey Amalfitano, Preston Gomez | Wrigley Field | |
| 1979 | Chicago Cubs | NL | East | 80 | 82 | .494 | 18.0 | 5 | Joey Amalfitano, Herman Franks | Wrigley Field | |
| 1978 | Chicago Cubs | NL | East | 79 | 83 | .488 | 11.0 | 3 | Herman Franks | Wrigley Field | |
| 1977 | Chicago Cubs | NL | East | 81 | 81 | .500 | 20.0 | 4 | Herman Franks | Wrigley Field | |
| 1976 | Chicago Cubs | NL | East | 75 | 87 | .463 | 26.0 | 4 | Jim Marshall | Wrigley Field | |
| 1975 | Chicago Cubs | NL | East | 75 | 87 | .463 | 17.5 | 6 | Jim Marshall | Wrigley Field | |
| 1974 | Chicago Cubs | NL | East | 66 | 96 | .407 | 22.0 | 6 | Jim Marshall, Whitey Lockman | Wrigley Field | |
| 1973 | Chicago Cubs | NL | East | 77 | 84 | .478 | 5.0 | 5 | Whitey Lockman | Wrigley Field | |
| 1972 | Chicago Cubs | NL | East | 85 | 70 | .548 | 11.0 | 2 | Whitey Lockman, Leo Durocher | Wrigley Field | |
| 1971 | Chicago Cubs | NL | East | 83 | 79 | .512 | 14.0 | 4 | Leo Durocher | Wrigley Field | |
| 1970 | Chicago Cubs | NL | East | 84 | 78 | .519 | 5.0 | 2 | Leo Durocher | Wrigley Field | |
| 1969 | Chicago Cubs | NL | East | 92 | 70 | .568 | 8.0 | 2 | Leo Durocher | Wrigley Field | |
| 1968 | Chicago Cubs | NL | - | 84 | 78 | .519 | 13.0 | 3 | Leo Durocher | Wrigley Field | |
| 1967 | Chicago Cubs | NL | - | 87 | 74 | .540 | 14.0 | 3 | Leo Durocher | Wrigley Field | |
| 1966 | Chicago Cubs | NL | - | 59 | 103 | .364 | 36.0 | 10 | Leo Durocher | Wrigley Field | |
| 1965 | Chicago Cubs | NL | - | 72 | 90 | .444 | 25.0 | 8 | Bob Kennedy, Lou Klein | Wrigley Field | |
| 1964 | Chicago Cubs | NL | - | 76 | 86 | .469 | 17.0 | 8 | Bob Kennedy | Wrigley Field | |
| 1963 | Chicago Cubs | NL | - | 82 | 80 | .506 | 17.0 | 7 | Bob Kennedy | Wrigley Field | |
| 1962 | Chicago Cubs | NL | - | 59 | 103 | .364 | 42.5 | 9 | El Tappe, Lou Klein, Charlie Metro | Wrigley Field | |
| 1961 | Chicago Cubs | NL | - | 64 | 90 | .416 | 29.0 | 7 | Lou Klein, Harry Craft, Vedie Himsl, El Tappe | Wrigley Field | |
| 1960 | Chicago Cubs | NL | - | 60 | 94 | .390 | 35.0 | 7 | Charlie Grimm, Lou Boudreau | Wrigley Field | |
| 1959 | Chicago Cubs | NL | - | 74 | 80 | .481 | 13.0 | 6 | Bob Scheffing | Wrigley Field | |
| 1958 | Chicago Cubs | NL | - | 72 | 82 | .468 | 20.0 | 6 | Bob Scheffing | Wrigley Field | |
| 1957 | Chicago Cubs | NL | - | 62 | 92 | .403 | 33.0 | 8 | Bob Scheffing | Wrigley Field | |
| 1956 | Chicago Cubs | NL | - | 60 | 94 | .390 | 33.0 | 8 | Stan Hack | Wrigley Field | |
| 1955 | Chicago Cubs | NL | - | 72 | 81 | .471 | 26.0 | 6 | Stan Hack | Wrigley Field | |
| 1954 | Chicago Cubs | NL | - | 64 | 90 | .416 | 33.0 | 7 | Stan Hack | Wrigley Field | |
| 1953 | Chicago Cubs | NL | - | 65 | 89 | .422 | 40.0 | 7 | Phil Cavarretta | Wrigley Field | |
| 1952 | Chicago Cubs | NL | - | 77 | 77 | .500 | 19.5 | 5 | Phil Cavarretta | Wrigley Field | |
| 1951 | Chicago Cubs | NL | - | 62 | 92 | .403 | 34.5 | 8 | Phil Cavarretta, Frankie Frisch | Wrigley Field | |
| 1950 | Chicago Cubs | NL | - | 64 | 89 | .418 | 26.5 | 7 | Frankie Frisch | Wrigley Field | |
| 1949 | Chicago Cubs | NL | - | 61 | 93 | .396 | 36.0 | 8 | Charlie Grimm, Frankie Frisch | Wrigley Field | |
| 1948 | Chicago Cubs | NL | - | 64 | 90 | .416 | 27.5 | 8 | Charlie Grimm | Wrigley Field | |
| 1947 | Chicago Cubs | NL | - | 69 | 85 | .448 | 25.0 | 6 | Charlie Grimm | Wrigley Field | |
| 1946 | Chicago Cubs | NL | - | 82 | 71 | .536 | 14.5 | 3 | Charlie Grimm | Wrigley Field | |
| 1945 | Chicago Cubs | NL | - | 98 | 56 | .636 | - | 1 | Charlie Grimm | Wrigley Field | Lost World Series (Tigers) |
| 1944 | Chicago Cubs | NL | - | 75 | 79 | .487 | 30.0 | 4 | Roy Johnson, Jimmie Wilson, Charlie Grimm | Wrigley Field | |
| 1943 | Chicago Cubs | NL | - | 74 | 79 | .484 | 30.5 | 5 | Jimmie Wilson | Wrigley Field | |
| 1942 | Chicago Cubs | NL | - | 68 | 86 | .442 | 38.0 | 6 | Jimmie Wilson | Wrigley Field | |
| 1941 | Chicago Cubs | NL | - | 70 | 84 | .455 | 30.0 | 6 | Jimmie Wilson | Wrigley Field | |
| 1940 | Chicago Cubs | NL | - | 75 | 79 | .487 | 25.5 | 5 | Gabby Hartnett | Wrigley Field | |
| 1939 | Chicago Cubs | NL | - | 84 | 70 | .545 | 13.0 | 4 | Gabby Hartnett | Wrigley Field | |
| 1938 | Chicago Cubs | NL | - | 89 | 63 | .586 | - | 1 | Gabby Hartnett, Charlie Grimm | Wrigley Field | Lost World Series (Yankees) |
| 1937 | Chicago Cubs | NL | - | 93 | 61 | .604 | 3.0 | 2 | Charlie Grimm | Wrigley Field | |
| 1936 | Chicago Cubs | NL | - | 87 | 67 | .565 | 5.0 | 3 | Charlie Grimm | Wrigley Field | |
| 1935 | Chicago Cubs | NL | - | 100 | 54 | .649 | - | 1 | Charlie Grimm | Wrigley Field | Lost World Series (Tigers) |
| 1934 | Chicago Cubs | NL | - | 86 | 65 | .570 | 8.0 | 3 | Charlie Grimm | Wrigley Field | |
| 1933 | Chicago Cubs | NL | - | 86 | 68 | .558 | 6.0 | 3 | Charlie Grimm | Wrigley Field | |
| 1932 | Chicago Cubs | NL | - | 90 | 64 | .584 | - | 1 | Charlie Grimm, Rogers Hornsby | Wrigley Field | Lost World Series (Yankees) |
| 1931 | Chicago Cubs | NL | - | 84 | 70 | .545 | 17.0 | 3 | Rogers Hornsby | Wrigley Field | |
| 1930 | Chicago Cubs | NL | - | 90 | 64 | .584 | 2.0 | 2 | Rogers Hornsby, Joe McCarthy | Wrigley Field | |
| 1929 | Chicago Cubs | NL | - | 98 | 54 | .645 | - | 1 | Joe McCarthy | Wrigley Field | Lost World Series (Athletics) |
| 1928 | Chicago Cubs | NL | - | 91 | 63 | .591 | 4.0 | 3 | Joe McCarthy | Wrigley Field | |
| 1927 | Chicago Cubs | NL | - | 85 | 68 | .556 | 8.5 | 4 | Joe McCarthy | Wrigley Field | |
| 1926 | Chicago Cubs | NL | - | 82 | 72 | .532 | 7.0 | 4 | Joe McCarthy | Wrigley Field | |
| 1925 | Chicago Cubs | NL | - | 68 | 86 | .442 | 27.5 | 8 | George Gibson, Rabbit Maranville, Bill Killefer | Wrigley Field | |
| 1924 | Chicago Cubs | NL | - | 81 | 72 | .529 | 12.0 | 5 | Bill Killefer | Wrigley Field | |
| 1923 | Chicago Cubs | NL | - | 83 | 71 | .539 | 12.5 | 4 | Bill Killefer | Wrigley Field | |
| 1922 | Chicago Cubs | NL | - | 80 | 74 | .519 | 13.0 | 5 | Bill Killefer | Wrigley Field | |
| 1921 | Chicago Cubs | NL | - | 64 | 89 | .418 | 30.0 | 7 | Bill Killefer, Johnny Evers | Wrigley Field | |
| 1920 | Chicago Cubs | NL | - | 75 | 79 | .487 | 18.0 | 6 | Fred Mitchell | Wrigley Field | |
| 1919 | Chicago Cubs | NL | - | 75 | 65 | .536 | 21.0 | 3 | Fred Mitchell | Wrigley Field | |
| 1918 | Chicago Cubs | NL | - | 84 | 45 | .651 | - | 1 | Fred Mitchell | Wrigley Field | Lost World Series (Red Sox) |
| 1917 | Chicago Cubs | NL | - | 74 | 80 | .481 | 24.0 | 5 | Fred Mitchell | Wrigley Field | |
| 1916 | Chicago Cubs | NL | - | 67 | 86 | .438 | 26.5 | 5 | Joe Tinker | Wrigley Field | |
| 1915 | Chicago Cubs | NL | - | 73 | 80 | .477 | 17.5 | 4 | Roger Bresnahan | West Side Grounds | |
| 1914 | Chicago Cubs | NL | - | 78 | 76 | .506 | 16.5 | 4 | Hank O'Day | West Side Grounds | |
| 1913 | Chicago Cubs | NL | - | 88 | 65 | .575 | 13.5 | 3 | Johnny Evers | West Side Grounds | |
| 1912 | Chicago Cubs | NL | - | 91 | 59 | .607 | 11.5 | 3 | Frank Chance | West Side Grounds | |
| 1911 | Chicago Cubs | NL | - | 92 | 62 | .597 | 7.5 | 2 | Frank Chance | West Side Grounds | |
| 1910 | Chicago Cubs | NL | - | 104 | 50 | .675 | - | 1 | Frank Chance | West Side Grounds | Lost World Series (Athletics) |
| 1909 | Chicago Cubs | NL | - | 104 | 49 | .680 | 6.5 | 2 | Frank Chance | West Side Grounds | |
| 1908 | Chicago Cubs | NL | - | 99 | 55 | .643 | - | 1 | Frank Chance | West Side Grounds | Won World Series (Tigers) |
| 1907 | Chicago Cubs | NL | - | 107 | 45 | .704 | - | 1 | Frank Chance | West Side Grounds | Won World Series (Tigers) |
| 1906 | Chicago Cubs | NL | - | 116 | 36 | .763 | - | 1 | Frank Chance | West Side Grounds | Lost World Series (White Sox) |
| 1905 | Chicago Cubs | NL | - | 92 | 61 | .601 | 13.0 | 3 | Frank Selee, Frank Chance | West Side Grounds | |
| 1904 | Chicago Cubs | NL | - | 93 | 60 | .608 | 13.0 | 2 | Frank Selee | West Side Grounds | |
| 1903 | Chicago Cubs | NL | - | 82 | 56 | .594 | 8.0 | 3 | Frank Selee | West Side Grounds | |
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