| Year | Team Name | League | Division | W | L | Pct | Rank | Managers | Stadium | Top Draft Pick | Playoffs | |
| 2013 | Chi Cubs | Cubs | MLB-NL | Central | 18 | 26 | .409 | 4 | Dale Sveum | Wrigley Field | dnq | |
| 2012 | Chi Cubs | Cubs | MLB-NL | Central | 61 | 101 | .377 | 5 | Dale Sveum | Wrigley Field | Albert Almora (#6) | dnq |
| 2011 | Chi Cubs | Cubs | MLB-NL | Central | 71 | 91 | .438 | 5 | Mike Quade | Wrigley Field | Javier Baez (#9) | dnq |
| 2010 | Chi Cubs | Cubs | MLB-NL | Central | 75 | 87 | .463 | 5 | Lou Piniella Mike Quade | Wrigley Field | Hayden Simpson (#16) | dnq |
| 2009 | Chi Cubs | Cubs | MLB-NL | Central | 83 | 78 | .516 | 2 | Lou Piniella | Wrigley Field | Brett Jackson (#31) | dnq |
| 2008 | Chi Cubs | Cubs | MLB-NL | Central | 97 | 64 | .602 | 1 | Lou Piniella | Wrigley Field | Andrew Cashner (#19) | Lost in NLDS (Los Angeles) |
| 2007 | Chi Cubs | Cubs | MLB-NL | Central | 85 | 77 | .525 | 1 | Lou Piniella | Wrigley Field | Josh Vitters (#3) | Lost in NLDS (Arizona) |
| 2006 | Chi Cubs | Cubs | MLB-NL | Central | 66 | 96 | .407 | 6 | Dusty Baker | Wrigley Field | Tyler Colvin (#13) | dnq |
| 2005 | Chi Cubs | Cubs | MLB-NL | Central | 79 | 83 | .488 | 4 | Dusty Baker | Wrigley Field | Mark Pawelek (#20) | dnq |
| 2004 | Chi Cubs | Cubs | MLB-NL | Central | 89 | 73 | .549 | 3 | Dusty Baker | Wrigley Field | Grant Johnson (#66) | dnq |
| 2003 | Chi Cubs | Cubs | MLB-NL | Central | 88 | 74 | .543 | 1 | Dusty Baker | Wrigley Field | Ryan Harvey (#6) | Lost NLCS (Marlins) |
| 2002 | Chi Cubs | Cubs | MLB-NL | Central | 67 | 95 | .414 | 5 | Don Baylor Bruce Kimm | Wrigley Field | Bobby Brownlie (#21) | dnq |
| 2001 | Chi Cubs | Cubs | MLB-NL | Central | 88 | 74 | .543 | 3 | Don Baylor | Wrigley Field | Mark Prior (#2) | dnq |
| 2000 | Chi Cubs | Cubs | MLB-NL | Central | 65 | 97 | .401 | 6 | Don Baylor | Wrigley Field | Lou Montanez (#3) | dnq |
| 1999 | Chi Cubs | Cubs | MLB-NL | Central | 67 | 95 | .414 | 6 | Jim Riggleman | Wrigley Field | Ben Christensen (#26) | dnq |
| 1998 | Chi Cubs | Cubs | MLB-NL | Central | 90 | 73 | .552 | 2 | Jim Riggleman | Wrigley Field | Corey Patterson (#3) | Lost in 1st Round (Braves) |
| 1997 | Chi Cubs | Cubs | MLB-NL | Central | 68 | 94 | .420 | 5 | Jim Riggleman | Wrigley Field | Jon Garland (#10) | dnq |
| 1996 | Chi Cubs | Cubs | MLB-NL | Central | 76 | 86 | .469 | 4 | Jim Riggleman | Wrigley Field | Todd Noel (#17) | dnq |
| 1995 | Chi Cubs | Cubs | MLB-NL | Central | 73 | 71 | .507 | 3 | Jim Riggleman | Wrigley Field | Kerry Wood (#4) | dnq |
| 1994 | Chi Cubs | Cubs | MLB-NL | Central | 49 | 64 | .434 | 5 | Tom Trebelhorn | Wrigley Field | Jayson Peterson (#15) | dnq |
| 1993 | Chi Cubs | Cubs | MLB-NL | East | 84 | 78 | .519 | 4 | Jim Lefebvre | Wrigley Field | Brooks Kieschnick (#10) | dnq |
| 1992 | Chi Cubs | Cubs | MLB-NL | East | 78 | 84 | .481 | 4 | Jim Lefebvre | Wrigley Field | Derek Wallace (#11) | dnq |
| 1991 | Chi Cubs | Cubs | MLB-NL | East | 77 | 83 | .481 | 4 | Jim Essian Don Zimmer Joe Altobelli | Wrigley Field | Doug Glanville (#12) | dnq |
| 1990 | Chi Cubs | Cubs | MLB-NL | East | 77 | 85 | .475 | 5 | Don Zimmer | Wrigley Field | Lance Dickson (#23) | dnq |
| 1989 | Chi Cubs | Cubs | MLB-NL | East | 93 | 69 | .574 | 1 | Don Zimmer | Wrigley Field | Earl Cunningham (#8) | Lost NLCS (Giants) |
| 1988 | Chi Cubs | Cubs | MLB-NL | East | 77 | 85 | .475 | 4 | Don Zimmer | Wrigley Field | Ty Griffin (#9) | dnq |
| 1987 | Chi Cubs | Cubs | MLB-NL | East | 76 | 85 | .472 | 6 | Gene Michael Frank Lucchesi | Wrigley Field | Mike Harkey (#4) | dnq |
| 1986 | Chi Cubs | Cubs | MLB-NL | East | 70 | 90 | .438 | 5 | Gene Michael Jim Frey John Vukovich | Wrigley Field | Derrick May (#9) | dnq |
| 1985 | Chi Cubs | Cubs | MLB-NL | East | 77 | 84 | .478 | 4 | Jim Frey | Wrigley Field | Rafael Palmeiro (#22) | dnq |
| 1984 | Chi Cubs | Cubs | MLB-NL | East | 96 | 65 | .596 | 1 | Jim Frey | Wrigley Field | Drew Hall (#3) | Lost NLCS (Padres) |
| 1983 | Chi Cubs | Cubs | MLB-NL | East | 71 | 91 | .438 | 5 | Lee Elia Charlie Fox | Wrigley Field | Jackie Davidson (#6) | dnq |
| 1982 | Chi Cubs | Cubs | MLB-NL | East | 73 | 89 | .451 | 5 | Lee Elia | Wrigley Field | Shawon Dunston (#1) | dnq |
| 1981 | Chi Cubs | Cubs | MLB-NL | East | 38 | 65 | .369 | Joey Amalfitano | Wrigley Field | Joe Carter (#2) | dnq | |
| 1980 | Chi Cubs | Cubs | MLB-NL | East | 64 | 98 | .395 | 6 | Preston Gomez Joey Amalfitano | Wrigley Field | Don Schulze (#11) | dnq |
| 1979 | Chi Cubs | Cubs | MLB-NL | East | 80 | 82 | .494 | 5 | Herman Franks Joey Amalfitano | Wrigley Field | Jon Perlman (#12) | dnq |
| 1978 | Chi Cubs | Cubs | MLB-NL | East | 79 | 83 | .488 | 3 | Herman Franks | Wrigley Field | Bill Hayes (#13) | dnq |
| 1977 | Chi Cubs | Cubs | MLB-NL | East | 81 | 81 | .500 | 4 | Herman Franks | Wrigley Field | Randy Martz (#12) | dnq |
| 1976 | Chi Cubs | Cubs | MLB-NL | East | 75 | 87 | .463 | 4 | Jim Marshall | Wrigley Field | Herman Segelke (#7) | dnq |
| 1975 | Chi Cubs | Cubs | MLB-NL | East | 75 | 87 | .463 | 6 | Jim Marshall | Wrigley Field | Brian Rosinski (#4) | dnq |
| 1974 | Chi Cubs | Cubs | MLB-NL | East | 66 | 96 | .407 | 6 | Whitey Lockman Jim Marshall | Wrigley Field | Scot Thompson (#7) | dnq |
| 1973 | Chi Cubs | Cubs | MLB-NL | East | 77 | 84 | .478 | 5 | Whitey Lockman | Wrigley Field | Jerry Tabb (#16) | dnq |
| 1972 | Chi Cubs | Cubs | MLB-NL | East | 85 | 70 | .548 | 2 | Leo Durocher Whitey Lockman | Wrigley Field | Brian Vernoy (#15) | dnq |
| 1971 | Chi Cubs | Cubs | MLB-NL | East | 83 | 79 | .512 | 4 | Leo Durocher | Wrigley Field | Jeff Wehmeier (#16) | dnq |
| 1970 | Chi Cubs | Cubs | MLB-NL | East | 84 | 78 | .519 | 2 | Leo Durocher | Wrigley Field | Gene Hiser (#19) | dnq |
| 1969 | Chi Cubs | Cubs | MLB-NL | East | 92 | 70 | .568 | 2 | Leo Durocher | Wrigley Field | Roger Metzger (#16) | dnq |
| 1968 | Chi Cubs | Cubs | MLB-NL | - | 84 | 78 | .519 | 3 | Leo Durocher | Wrigley Field | Ralph Rickey (#15) | dnq |
| 1967 | Chi Cubs | Cubs | MLB-NL | - | 87 | 74 | .540 | 3 | Leo Durocher | Wrigley Field | Terry Hughes (#2) | dnq |
| 1966 | Chi Cubs | Cubs | MLB-NL | - | 59 | 103 | .364 | 10 | Leo Durocher | Wrigley Field | Dean Burk (#5) | dnq |
| 1965 | Chi Cubs | Cubs | MLB-NL | - | 72 | 90 | .444 | 8 | Lou Klein Bob Kennedy | Wrigley Field | Rick James (#6) | dnq |
| 1964 | Chi Cubs | Cubs | MLB-NL | - | 76 | 86 | .469 | 8 | Bob Kennedy | Wrigley Field | dnq | |
| 1963 | Chi Cubs | Cubs | MLB-NL | - | 82 | 80 | .506 | 7 | Bob Kennedy | Wrigley Field | dnq | |
| 1962 | Chi Cubs | Cubs | MLB-NL | - | 59 | 103 | .364 | 9 | Charlie Metro Lou Klein El Tappe | Wrigley Field | dnq | |
| 1961 | Chi Cubs | Cubs | MLB-NL | - | 64 | 90 | .416 | 7 | El Tappe Vedie Himsl Harry Craft Lou Klein | Wrigley Field | dnq | |
| 1960 | Chi Cubs | Cubs | MLB-NL | - | 60 | 94 | .390 | 7 | Lou Boudreau Charlie Grimm | Wrigley Field | dnq | |
| 1959 | Chi Cubs | Cubs | MLB-NL | - | 74 | 80 | .481 | 6 | Bob Scheffing | Wrigley Field | dnq | |
| 1958 | Chi Cubs | Cubs | MLB-NL | - | 72 | 82 | .468 | 6 | Bob Scheffing | Wrigley Field | dnq | |
| 1957 | Chi Cubs | Cubs | MLB-NL | - | 62 | 92 | .403 | 8 | Bob Scheffing | Wrigley Field | dnq | |
| 1956 | Chi Cubs | Cubs | MLB-NL | - | 60 | 94 | .390 | 8 | Stan Hack | Wrigley Field | dnq | |
| 1955 | Chi Cubs | Cubs | MLB-NL | - | 72 | 81 | .471 | 6 | Stan Hack | Wrigley Field | dnq | |
| 1954 | Chi Cubs | Cubs | MLB-NL | - | 64 | 90 | .416 | 7 | Stan Hack | Wrigley Field | dnq | |
| 1953 | Chi Cubs | Cubs | MLB-NL | - | 65 | 89 | .422 | 7 | Phil Cavarretta | Wrigley Field | dnq | |
| 1952 | Chi Cubs | Cubs | MLB-NL | - | 77 | 77 | .500 | 5 | Phil Cavarretta | Wrigley Field | dnq | |
| 1951 | Chi Cubs | Cubs | MLB-NL | - | 62 | 92 | .403 | 8 | Phil Cavarretta Frankie Frisch | Wrigley Field | dnq | |
| 1950 | Chi Cubs | Cubs | MLB-NL | - | 64 | 89 | .418 | 7 | Frankie Frisch | Wrigley Field | dnq | |
| 1949 | Chi Cubs | Cubs | MLB-NL | - | 61 | 93 | .396 | 8 | Frankie Frisch Charlie Grimm | Wrigley Field | dnq | |
| 1948 | Chi Cubs | Cubs | MLB-NL | - | 64 | 90 | .416 | 8 | Charlie Grimm | Wrigley Field | dnq | |
| 1947 | Chi Cubs | Cubs | MLB-NL | - | 69 | 85 | .448 | 6 | Charlie Grimm | Wrigley Field | dnq | |
| 1946 | Chi Cubs | Cubs | MLB-NL | - | 82 | 71 | .536 | 3 | Charlie Grimm | Wrigley Field | dnq | |
| 1945 | Chi Cubs | Cubs | MLB-NL | - | 98 | 56 | .636 | 1 | Charlie Grimm | Wrigley Field | Lost World Series (Tigers) | |
| 1944 | Chi Cubs | Cubs | MLB-NL | - | 75 | 79 | .487 | 4 | Charlie Grimm Jimmie Wilson Roy Johnson | Wrigley Field | dnq | |
| 1943 | Chi Cubs | Cubs | MLB-NL | - | 74 | 79 | .484 | 5 | Jimmie Wilson | Wrigley Field | dnq | |
| 1942 | Chi Cubs | Cubs | MLB-NL | - | 68 | 86 | .442 | 6 | Jimmie Wilson | Wrigley Field | dnq | |
| 1941 | Chi Cubs | Cubs | MLB-NL | - | 70 | 84 | .455 | 6 | Jimmie Wilson | Wrigley Field | dnq | |
| 1940 | Chi Cubs | Cubs | MLB-NL | - | 75 | 79 | .487 | 5 | Gabby Hartnett | Wrigley Field | dnq | |
| 1939 | Chi Cubs | Cubs | MLB-NL | - | 84 | 70 | .545 | 4 | Gabby Hartnett | Wrigley Field | dnq | |
| 1938 | Chi Cubs | Cubs | MLB-NL | - | 89 | 63 | .586 | 1 | Charlie Grimm Gabby Hartnett | Wrigley Field | Lost World Series (Yankees) | |
| 1937 | Chi Cubs | Cubs | MLB-NL | - | 93 | 61 | .604 | 2 | Charlie Grimm | Wrigley Field | dnq | |
| 1936 | Chi Cubs | Cubs | MLB-NL | - | 87 | 67 | .565 | 3 | Charlie Grimm | Wrigley Field | dnq | |
| 1935 | Chi Cubs | Cubs | MLB-NL | - | 100 | 54 | .649 | 1 | Charlie Grimm | Wrigley Field | Lost World Series (Tigers) | |
| 1934 | Chi Cubs | Cubs | MLB-NL | - | 86 | 65 | .570 | 3 | Charlie Grimm | Wrigley Field | dnq | |
| 1933 | Chi Cubs | Cubs | MLB-NL | - | 86 | 68 | .558 | 3 | Charlie Grimm | Wrigley Field | dnq | |
| 1932 | Chi Cubs | Cubs | MLB-NL | - | 90 | 64 | .584 | 1 | Rogers Hornsby Charlie Grimm | Wrigley Field | Lost World Series (Yankees) | |
| 1931 | Chi Cubs | Cubs | MLB-NL | - | 84 | 70 | .545 | 3 | Rogers Hornsby | Wrigley Field | dnq | |
| 1930 | Chi Cubs | Cubs | MLB-NL | - | 90 | 64 | .584 | 2 | Joe McCarthy Rogers Hornsby | Wrigley Field | dnq | |
| 1929 | Chi Cubs | Cubs | MLB-NL | - | 98 | 54 | .645 | 1 | Joe McCarthy | Wrigley Field | Lost World Series (Athletics) | |
| 1928 | Chi Cubs | Cubs | MLB-NL | - | 91 | 63 | .591 | 3 | Joe McCarthy | Wrigley Field | dnq | |
| 1927 | Chi Cubs | Cubs | MLB-NL | - | 85 | 68 | .556 | 4 | Joe McCarthy | Wrigley Field | dnq | |
| 1926 | Chi Cubs | Cubs | MLB-NL | - | 82 | 72 | .532 | 4 | Joe McCarthy | Cubs Park | dnq | |
| 1925 | Chi Cubs | Cubs | MLB-NL | - | 68 | 86 | .442 | 8 | Bill Killefer Rabbit Maranville George Gibson | Cubs Park | dnq | |
| 1924 | Chi Cubs | Cubs | MLB-NL | - | 81 | 72 | .529 | 5 | Bill Killefer | Cubs Park | dnq | |
| 1923 | Chi Cubs | Cubs | MLB-NL | - | 83 | 71 | .539 | 4 | Bill Killefer | Cubs Park | dnq | |
| 1922 | Chi Cubs | Cubs | MLB-NL | - | 80 | 74 | .519 | 5 | Bill Killefer | Cubs Park | dnq | |
| 1921 | Chi Cubs | Cubs | MLB-NL | - | 64 | 89 | .418 | 7 | Johnny Evers Bill Killefer | Cubs Park | dnq | |
| 1920 | Chi Cubs | Cubs | MLB-NL | - | 75 | 79 | .487 | 6 | Fred Mitchell | Cubs Park | dnq | |
| 1919 | Chi Cubs | Cubs | MLB-NL | - | 75 | 65 | .536 | 3 | Fred Mitchell | Weeghman Park | dnq | |
| 1918 | Chi Cubs | Cubs | MLB-NL | - | 84 | 45 | .651 | 1 | Fred Mitchell | Weeghman Park | Lost World Series (Red Sox) | |
| 1917 | Chi Cubs | Cubs | MLB-NL | - | 74 | 80 | .481 | 5 | Fred Mitchell | Weeghman Park | dnq | |
| 1916 | Chi Cubs | Cubs | MLB-NL | - | 67 | 86 | .438 | 5 | Joe Tinker | Weeghman Park | dnq | |
| 1915 | Chi Cubs | Cubs | MLB-NL | - | 73 | 80 | .477 | 4 | Roger Bresnahan | West Side Park | dnq | |
| 1914 | Chi Cubs | Cubs | MLB-NL | - | 78 | 76 | .506 | 4 | Hank O'Day | West Side Park | dnq | |
| 1913 | Chi Cubs | Cubs | MLB-NL | - | 88 | 65 | .575 | 3 | Johnny Evers | West Side Park | dnq | |
| 1912 | Chi Cubs | Cubs | MLB-NL | - | 91 | 59 | .607 | 3 | Frank Chance | West Side Park | dnq | |
| 1911 | Chi Cubs | Cubs | MLB-NL | - | 92 | 62 | .597 | 2 | Frank Chance | West Side Park | dnq | |
| 1910 | Chi Cubs | Cubs | MLB-NL | - | 104 | 50 | .675 | 1 | Frank Chance | West Side Park | Lost World Series (Athletics) | |
| 1909 | Chi Cubs | Cubs | MLB-NL | - | 104 | 49 | .680 | 2 | Frank Chance | West Side Park | dnq | |
| 1908 | Chi Cubs | Cubs | MLB-NL | - | 99 | 55 | .643 | 1 | Frank Chance | West Side Park | Won World Series (Tigers) | |
| 1907 | Chi Cubs | Cubs | MLB-NL | - | 107 | 45 | .704 | 1 | Frank Chance | West Side Park | Won World Series (Tigers) | |
| 1906 | Chi Cubs | Cubs | MLB-NL | - | 116 | 36 | .763 | 1 | Frank Chance | West Side Park | Lost World Series (White Sox) | |
| 1905 | Chi Cubs | Cubs | MLB-NL | - | 92 | 61 | .601 | 3 | Frank Chance Frank Selee | West Side Park | dnq | |
| 1904 | Chi Cubs | Cubs | MLB-NL | - | 93 | 60 | .608 | 2 | Frank Selee | West Side Park | dnq | |
| 1903 | Chi Cubs | Cubs | MLB-NL | - | 82 | 56 | .594 | 3 | Frank Selee | West Side Park | dnq | |