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| 2 World Series championship seasons: 1907, 1908 |
| Last World Series championship: 1908, 104 seasons ago |
| Chicago Orphans became Chicago Cubs in 1903 |
| Best finish: |
| beat Detroit in World Series in 1907 season |
| beat Detroit in World Series in 1908 season |
| TEAM | SEASON | RECORD | PERC | DIV STAND | GB | LEAGUE | PLAYOFFS |
| Chi Orphans | 1901 | 53-86 | .381 | 6th NL | -37.0 | ||
| Chi Orphans | 1902 | 68-69 | .496 | 5th NL | -34.0 | ||
| Chi Cubs | 1903 | 82-56 | .594 | 3rd NL | - 8.0 | ||
| Chi Cubs | 1904 | 93-60 | .608 | 2nd NL | -13.0 | ||
| Chi Cubs | 1905 | 92-61 | .601 | 3rd NL | -13.0 | ||
| Chi Cubs | 1906 | 116-36 | .763 | 1st NL | +20.0 | LChW | |
| %Chi Cubs | 1907 | 107-45 | .704 | 1st NL | +17.0 | WDet | |
| %Chi Cubs | 1908 | 99-55 | .643 | 1st NL | + 1.0 | WDet | |
| Chi Cubs | 1909 | 104-49 | .680 | 2nd NL | - 6.5 | ||
| Chi Cubs | 1910 | 104-50 | .675 | 1st NL | +13.0 | LPhA | |
| Chi Cubs | 1911 | 92-62 | .597 | 2nd NL | - 7.5 | ||
| Chi Cubs | 1912 | 91-59 | .607 | 3rd NL | -11.5 | ||
| Chi Cubs | 1913 | 88-65 | .575 | 3rd NL | -13.5 | ||
| Chi Cubs | 1914 | 78-76 | .506 | 4th NL | -16.5 | ||
| Chi Cubs | 1915 | 73-80 | .477 | 4th NL | -17.5 | ||
| Chi Cubs | 1916 | 67-86 | .438 | 5th NL | -26.5 | ||
| Chi Cubs | 1917 | 74-80 | .481 | 5th NL | -24.0 | ||
| Chi Cubs | 1918 | 84-45 | .651 | 1st NL | +10.5 | LBos | |
| Chi Cubs | 1919 | 75-65 | .536 | 3rd NL | -21.0 | ||
| Chi Cubs | 1920 | 75-79 | .487 | T5th NL | -18.0 | ||
| Chi Cubs | 1921 | 64-89 | .418 | 7th NL | -30.0 | ||
| Chi Cubs | 1922 | 80-74 | .519 | 5th NL | -13.0 | ||
| Chi Cubs | 1923 | 83-71 | .539 | 4th NL | -12.5 | ||
| Chi Cubs | 1924 | 81-72 | .529 | 5th NL | -12.0 | ||
| Chi Cubs | 1925 | 68-86 | .442 | 8th NL | -27.5 | ||
| Chi Cubs | 1926 | 82-72 | .532 | 4th NL | - 7.0 | ||
| Chi Cubs | 1927 | 85-68 | .556 | 4th NL | - 8.5 | ||
| Chi Cubs | 1928 | 91-63 | .591 | 3rd NL | - 4.0 | ||
| Chi Cubs | 1929 | 98-54 | .645 | 1st NL | +10.5 | LPhA | |
| Chi Cubs | 1930 | 90-64 | .584 | 2nd NL | - 2.0 | ||
| Chi Cubs | 1931 | 84-70 | .545 | 3rd NL | -17.0 | ||
| Chi Cubs | 1932 | 90-64 | .584 | 1st NL | + 4.0 | LNYY | |
| Chi Cubs | 1933 | 86-68 | .558 | 3rd NL | - 6.0 | ||
| Chi Cubs | 1934 | 86-65 | .570 | 3rd NL | - 8.0 | ||
| Chi Cubs | 1935 | 100-54 | .649 | 1st NL | + 4.0 | LDet | |
| Chi Cubs | 1936 | 87-67 | .565 | T2nd NL | - 5.0 | ||
| Chi Cubs | 1937 | 93-61 | .604 | 2nd NL | - 3.0 | ||
| Chi Cubs | 1938 | 89-63 | .586 | 1st NL | + 2.0 | LNYY | |
| Chi Cubs | 1939 | 84-70 | .545 | 4th NL | -13.0 | ||
| Chi Cubs | 1940 | 75-79 | .487 | 5th NL | -25.5 | ||
| Chi Cubs | 1941 | 70-84 | .455 | 6th NL | -30.0 | ||
| Chi Cubs | 1942 | 68-86 | .442 | 6th NL | -38.0 | ||
| Chi Cubs | 1943 | 74-79 | .484 | 5th NL | -30.5 | ||
| Chi Cubs | 1944 | 75-79 | .487 | 4th NL | -30.0 | ||
| Chi Cubs | 1945 | 98-56 | .636 | 1st NL | + 3.0 | LDet | |
| Chi Cubs | 1946 | 82-71 | .536 | 3rd NL | -14.5 | ||
| Chi Cubs | 1947 | 69-85 | .448 | 6th NL | -25.0 | ||
| Chi Cubs | 1948 | 64-90 | .416 | 8th NL | -27.5 | ||
| Chi Cubs | 1949 | 61-93 | .396 | 8th NL | -36.0 | ||
| Chi Cubs | 1950 | 64-89 | .418 | 7th NL | -26.5 | ||
| Chi Cubs | 1951 | 62-92 | .403 | 8th NL | -34.5 | ||
| Chi Cubs | 1952 | 77-77 | .500 | 5th NL | -19.5 | ||
| Chi Cubs | 1953 | 65-89 | .422 | 7th NL | -40.0 | ||
| Chi Cubs | 1954 | 64-90 | .416 | 7th NL | -33.0 | ||
| Chi Cubs | 1955 | 72-81 | .471 | 6th NL | -26.0 | ||
| Chi Cubs | 1956 | 60-94 | .390 | 8th NL | -33.0 | ||
| Chi Cubs | 1957 | 62-92 | .403 | T7th NL | -33.0 | ||
| Chi Cubs | 1958 | 72-82 | .468 | T5th NL | -20.0 | ||
| Chi Cubs | 1959 | 74-80 | .481 | T5th NL | -13.0 | ||
| Chi Cubs | 1960 | 60-94 | .390 | 7th NL | -35.0 | ||
| Chi Cubs | 1961 | 64-90 | .416 | 7th NL | -29.0 | ||
| Chi Cubs | 1962 | 59-103 | .364 | 9th NL | -42.5 | ||
| Chi Cubs | 1963 | 82-80 | .506 | 7th NL | -17.0 | ||
| Chi Cubs | 1964 | 76-86 | .469 | 8th NL | -17.0 | ||
| Chi Cubs | 1965 | 72-90 | .444 | 8th NL | -25.0 | ||
| Chi Cubs | 1966 | 59-103 | .364 | 10th NL | -36.0 | ||
| Chi Cubs | 1967 | 87-74 | .540 | 3rd NL | -14.0 | ||
| Chi Cubs | 1968 | 84-78 | .519 | 3rd NL | -13.0 | ||
| Chi Cubs | 1969 | 92-70 | .568 | 2nd NL East | - 8.0 | ||
| Chi Cubs | 1970 | 84-78 | .519 | 2nd NL East | - 5.0 | ||
| Chi Cubs | 1971 | 83-79 | .512 | T3rd NL East | -14.0 | ||
| Chi Cubs | 1972 | 85-70 | .548 | 2nd NL East | -11.0 | ||
| Chi Cubs | 1973 | 77-84 | .478 | 5th NL East | - 5.0 | ||
| Chi Cubs | 1974 | 66-96 | .407 | 6th NL East | -22.0 | ||
| Chi Cubs | 1975 | 75-87 | .463 | T5th NL East | -17.5 | ||
| Chi Cubs | 1976 | 75-87 | .463 | 4th NL East | -26.0 | ||
| Chi Cubs | 1977 | 81-81 | .500 | 4th NL East | -20.0 | ||
| Chi Cubs | 1978 | 79-83 | .488 | 3rd NL East | -11.0 | ||
| Chi Cubs | 1979 | 80-82 | .494 | 5th NL East | -18.0 | ||
| Chi Cubs | 1980 | 64-98 | .395 | 6th NL East | -27.0 | ||
| Chi Cubs | 1981a | 15-37 | .288 | 6th NL East | -17.5 | ||
| Chi Cubs | 1981b | 23-28 | .451 | 5th NL East | - 6.0 | ||
| Chi Cubs | 1982 | 73-89 | .451 | 5th NL East | -19.0 | ||
| Chi Cubs | 1983 | 71-91 | .438 | 5th NL East | -19.0 | ||
| Chi Cubs | 1984 | 96-65 | .596 | 1st NL East | + 6.5 | LSD | |
| Chi Cubs | 1985 | 77-84 | .478 | 4th NL East | -23.5 | ||
| Chi Cubs | 1986 | 70-90 | .438 | 5th NL East | -37.0 | ||
| Chi Cubs | 1987 | 76-85 | .472 | 6th NL East | -18.5 | ||
| Chi Cubs | 1988 | 77-85 | .475 | 4th NL East | -24.0 | ||
| Chi Cubs | 1989 | 93-69 | .574 | 1st NL East | + 6.0 | LSF | |
| Chi Cubs | 1990 | 77-85 | .475 | T4th NL East | -18.0 | ||
| Chi Cubs | 1991 | 77-83 | .481 | 4th NL East | -20.0 | ||
| Chi Cubs | 1992 | 78-84 | .481 | 4th NL East | -18.0 | ||
| Chi Cubs | 1993 | 84-78 | .519 | 4th NL East | -13.0 | ||
| Chi Cubs | 1994 | 49-64 | .434 | 5th NL Cent | -16.5 | 13th NL | |
| Chi Cubs | 1995 | 73-71 | .507 | 3rd NL Cent | -12.0 | 6th NL | |
| Chi Cubs | 1996 | 76-86 | .469 | 4th NL Cent | -12.0 | 8th NL | |
| Chi Cubs | 1997 | 68-94 | .420 | 5th NL Cent | -16.0 | T13th NL | |
| Chi Cubs | 1998 | 90-73 | .552 | 2nd NL Cent | -13.0 | 4th NL | LAtl |
| Chi Cubs | 1999 | 67-95 | .414 | 6th NL Cent | -30.0 | 15th NL | |
| Chi Cubs | 2000 | 65-97 | .401 | 6th NL Cent | -30.0 | T15th NL | |
| Chi Cubs | 2001 | 88-74 | .543 | 3rd NL Cent | - 5.0 | 6th NL | |
| Chi Cubs | 2002 | 67-95 | .414 | 5th NL Cent | -30.0 | 14th NL | |
| Chi Cubs | 2003 | 88-74 | .543 | 1st NL Cent | + 1.0 | 4th NL | WAtl LFlo |
| Chi Cubs | 2004 | 89-73 | .549 | 3rd NL Cent | -16.0 | 6th NL | |
| Chi Cubs | 2005 | 79-83 | .488 | 4th NL Cent | -21.0 | 10th NL | |
| Chi Cubs | 2006 | 66-96 | .407 | 6th NL Cent | -17.5 | 16th NL | |
| Chi Cubs | 2007 | 85-77 | .525 | 1st NL Cent | + 2.0 | 3rd NL | LAri |
| Chi Cubs | 2008 | 97-67 | .602 | 1st NL Cent | + 7.5 | 1st NL | LLAD |
| Chi Cubs | 2009 | 83-78 | .516 | 2nd NL Cent | - 7.5 | 8th NL | |
| Chi Cubs | 2010 | 75-87 | .463 | 5th NL Cent | -16.0 | 13th NL | |
| Chi Cubs | 2011 | 71-91 | .438 | 5th NL Cent | -25.0 | T14th NL | |
| Chi Cubs | 2012 | 61-101 | .377 | 5th NL Cent | -36.0 | 15th NL |