| Year | Team Name | League | Division | Affilate | W | L | Pct | Rank | Managers | Stadium | Playoffs | |
| 2013 | Kane County | Cougars | Midw | Western | CHC | 30 | 36 | .455 | 6 | Mark Johnson | Fifth Third Bank Ballpark | dnq |
| 2012 | Kane County | Cougars | Midw | Western | KC | 68 | 72 | .486 | 5 | Brian Buchanan | Fifth Third Bank Ballpark | dnq |
| 2011 | Kane County | Cougars | Midw | Western | KC | 65 | 74 | .468 | 5 | Vance Wilson | Elfstrom Stadium | Lost in Semi-Finals |
| 2010 | Kane County | Cougars | Midw | Western | OAK | 71 | 67 | .514 | 5 | Aaron Nieckula | Elfstrom Stadium | Lost in Semi-Finals |
| 2009 | Kane County | Cougars | Midw | Western | OAK | 76 | 64 | .543 | 3 | Steve Scarsone | Elfstrom Stadium | Lost in 1st Round |
| 2008 | Kane County | Cougars | Midw | Western | OAK | 72 | 66 | .522 | 4 | Aaron Nieckula | Elfstrom Stadium | Lost in 1st Round |
| 2007 | Kane County | Cougars | Midw | Western | OAK | 63 | 76 | .453 | 6 | Aaron Nieckula | Elfstrom Stadium | dnq |
| 2006 | Kane County | Cougars | Midw | Western | OAK | 79 | 60 | .568 | 1 | Aaron Nieckula | Elfstrom Stadium | Lost in Finals |
| 2005 | Kane County | Cougars | Midw | Western | OAK | 67 | 72 | .482 | 6 | Dave Joppie | Elfstrom Stadium | dnq |
| 2004 | Kane County | Cougars | Midw | Western | OAK | 83 | 56 | .597 | 1 | Dave Joppie | Elfstrom Stadium | Lost in Finals |
| 2003 | Kane County | Cougars | Midw | Western | OAK | 70 | 50 | .583 | 2 | Webster Garrison | Elfstrom Stadium | Lost in 1st Round |
| 2002 | Kane County | Cougars | Midw | Western | FLA | 64 | 75 | .460 | 5 | Steve Phillips | Elfstrom Stadium | dnq |
| 2001 | Kane County | Cougars | Midw | Western | FLA | 88 | 50 | .638 | 1 | Russ Morman | Elfstrom Stadium | Co-League Champions (South Bend) |
| 2000 | Kane County | Cougars | Midw | - | FLA | 74 | 65 | .532 | Russ Morman | Elfstrom Stadium | dnq | |
| 1999 | Kane County | Cougars | Midw | Central | FLA | 78 | 59 | .569 | 1 | Rich Renteria | Elfstrom Stadium | Lost in Semi-Finals |
| 1998 | Kane County | Cougars | Midw | Central | FLA | 69 | 71 | .493 | 4 | Juan Bustabad | Elfstrom Stadium | dnq |
| 1997 | Kane County | Cougars | Midw | Central | FLA | 70 | 68 | .507 | 2 | Lynn Jones | Elfstrom Stadium | Lost in Semi-Finals |
| 1996 | Kane County | Cougars | Midw | Central | FLA | 65 | 88 | .425 | 5 | Lynn Jones | Elfstrom Stadium | dnq |
| 1995 | Kane County | Cougars | Midw | Central | FLA | 69 | 69 | .500 | 3 | Lynn Jones | Elfstrom Stadium | Lost in 1st Round |
| 1994 | Kane County | Cougars | Midw | Northern | FLA | 71 | 68 | .511 | 6 | Lynn Jones | Elfstrom Stadium | dnq |
| 1993 | Kane County | Cougars | Midw | Northern | FLA | 75 | 62 | .547 | 4 | Carlos Tosca | Elfstrom Stadium | dnq |
| 1992 | Kane County | Cougars | Midw | Northern | BAL | 61 | 76 | .445 | 6 | Joel Youngblood | Elfstrom Stadium | dnq |
| 1991 | Kane County | Cougars | Midw | Northern | BAL | 68 | 67 | .504 | 5 | Bob Miscik | Elfstrom Stadium | Lost in Semi-Finals |