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| YEAR | DIVISION | W | L | PCT | GB | FINISH |
| 1988 | Rickey | 54 | 26 | .675 | —- | first |
| 1989 | Rickey | 43 | 37 | .538 | 3 | second |
| 1990 | Rickey | 49 | 31 | .613 | —- | first |
| 1991 | Rickey | 54 | 26 | .675 | —- | first |
| 1992 | Rickey | 57 | 23 | .713 | —- | first |
| 1993 | Rickey | 78 | 44 | .639 | —- | first |
| 1994 | Rickey | 99 | 61 | .619 | —- | first |
| 1995 | Rickey | 97 | 63 | .606 | —- | first |
| 1996 | Rickey | 94 | 66 | .588 | 8 | second |
| 1997 | Rickey | 80 | 80 | .500 | 13 | fourth |
| 1998 | Rickey | 70 | 92 | .432 | 39 | fourth |
| 1999 | Rickey | 88 | 74 | .543 | 15 | fourth |
| 2000 | Rickey | 86 | 76 | .531 | 15 | third |
| 2001 | Veeck | 76 | 86 | .469 | 36 | third |
| 2002 | Veeck | 69 | 93 | .426 | 41 | fourth |
| 2003 | Veeck | 69 | 93 | .426 | 50 | third |
| 2004 | Veeck | 92 | 70 | .568 | 17 | third |
| 2005 | Veeck | 82 | 80 | .506 | 15 | third |
| 2006 | Veeck | 71 | 91 | .438 | 40 | fifth |
| 2007 | Veeck | 96 | 66 | .593 | 2 | second |
| 2008 | Veeck | 61 | 101 | .377 | 45 | fourth |
| 2009 | Veeck | 54 | 108 | .333 | 54 | fifth |
| 2010 | Veeck | 91 | 71 | .562 | 7 | second |
| 2011 | Veeck | 50 | 112 | .309 | 67 | fifth |
| 2012 | Veeck | 97 | 65 | .599 | 8 | second |
| 2013 | Veeck | 68 | 94 | .420 | 38 | fifth |
| 2014 | Veeck | 85 | 77 | .525 | 14 | third |
| 2015 | Veeck | 90 | 72 | .556 | 4 | second |
| 2016 | Veeck | 101 | 61 | .623 | 9 | second |
| 2017 | Veeck | 79 | 83 | .488 | 25 | third |
| 2018 | Veeck | 88 | 74 | .543 | 29 | third |
| 2019 | Veeck | 74 | 88 | .457 | 29 | forth |
| 2020 | Veeck | 87 | 75 | .537 | 20 | third |
| 2021 | Veeck | 66 | 96 | .407 | 38 | fifth |
| 2022 | Veeck | 95 | 67 | .586 | 3 | second |
| 2023 | Veeck | 80 | 82 | .494 | 14 | third |