| 2020 | Kane County Cougars | Midw | - | 0 | 0 | 0 | | -- | 0 | 0 | 0 | Vince Harrison | | 0 | 0 | Northwestern Medicine Field | no info |
| 2019 | Kane County Cougars | Midw | Western | 139 | 81 | 58 | .583 | -- | 626 | 490 | 136 | Vince Harrison | | 350,305 | 0 | Northwestern Medicine Field | Lost in 1st Round |
| 2018 | Kane County Cougars | Midw | Western | 138 | 72 | 66 | .522 | 8.0 | 630 | 556 | 74 | Blake Lalli | | 350,028 | 0 | Northwestern Medicine Field | dnq |
| 2017 | Kane County Cougars | Midw | Western | 137 | 72 | 65 | .526 | 6.5 | 553 | 518 | 35 | Butch Hobson | | 394,567 | 0 | Northwestern Medicine Field | Lost in 1st Round |
| 2016 | Kane County Cougars | Midw | Western | 140 | 65 | 75 | .464 | 21.0 | 474 | 517 | -43 | Mike Benjamin | | 400,931 | 0 | Fifth Third Bank Ballpark | dnq |
| 2015 | Kane County Cougars | Midw | Western | 138 | 84 | 54 | .609 | 4.0 | 627 | 514 | 113 | Mark Grudzielanek | | 408,449 | 0 | Fifth Third Bank Ballpark | Lost in 1st Round |
| 2014 | Kane County Cougars | Midw | Western | 140 | 91 | 49 | .650 | -- | 647 | 449 | 198 | Mark Johnson | | 415,571 | 0 | Fifth Third Bank Ballpark | League Champions |
| 2013 | Kane County Cougars | Midw | Western | 135 | 55 | 80 | .407 | 31.5 | 582 | 708 | -126 | Mark Johnson | | 406,152 | 0 | Fifth Third Bank Ballpark | dnq |
| 2012 | Kane County Cougars | Midw | Western | 140 | 68 | 72 | .486 | 10.5 | 601 | 674 | -73 | Brian Buchanan | | 391,102 | 0 | Fifth Third Bank Ballpark | dnq |
| 2011 | Kane County Cougars | Midw | Western | 139 | 65 | 74 | .468 | 17.0 | 539 | 623 | -84 | Vance Wilson | | 410,262 | 0 | Elfstrom Stadium | Lost in Semi-Finals |
| 2010 | Kane County Cougars | Midw | Western | 138 | 71 | 67 | .514 | 12.0 | 669 | 618 | 51 | Aaron Nieckula | | 430,831 | 0 | Elfstrom Stadium | Lost in Semi-Finals |
| 2009 | Kane County Cougars | Midw | Western | 140 | 76 | 64 | .543 | 6.0 | 598 | 585 | 13 | Steve Scarsone | | 400,040 | 0 | Elfstrom Stadium | Lost in 1st Round |
| 2008 | Kane County Cougars | Midw | Western | 138 | 72 | 66 | .522 | 6.5 | 627 | 591 | 36 | Aaron Nieckula | | 472,596 | 0 | Elfstrom Stadium | Lost in 1st Round |
| 2007 | Kane County Cougars | Midw | Western | 139 | 63 | 76 | .453 | 15.5 | 589 | 593 | -4 | Aaron Nieckula | | 454,398 | 0 | Elfstrom Stadium | dnq |
| 2006 | Kane County Cougars | Midw | Western | 139 | 79 | 60 | .568 | -- | 720 | 616 | 104 | Aaron Nieckula | | 500,052 | 0 | Elfstrom Stadium | Lost in Finals |
| 2005 | Kane County Cougars | Midw | Western | 139 | 67 | 72 | .482 | 9.0 | 750 | 740 | 10 | Dave Joppie | | 518,394 | 0 | Elfstrom Stadium | dnq |
| 2004 | Kane County Cougars | Midw | Western | 139 | 83 | 56 | .597 | -- | 730 | 606 | 124 | Dave Joppie | | 522,042 | 0 | Elfstrom Stadium | Lost in Finals |
| 2003 | Kane County Cougars | Midw | Western | 120 | 70 | 50 | .583 | 8.0 | 542 | 528 | 14 | Webster Garrison | | 516,133 | 0 | Elfstrom Stadium | Lost in 1st Round |
| 2002 | Kane County Cougars | Midw | Western | 139 | 64 | 75 | .460 | 21.5 | 559 | 653 | -94 | Steve Phillips | | 510,390 | 0 | Elfstrom Stadium | dnq |
| 2001 | Kane County Cougars | Midw | Western | 138 | 88 | 50 | .638 | -- | 767 | 619 | 148 | Russ Morman | | 523,222 | 0 | Elfstrom Stadium | Co-League Champions (South Bend) |
| 2000 | Kane County Cougars | Midw | - | 139 | 74 | 65 | .532 | -- | 586 | 571 | 15 | Russ Morman | | 0 | 0 | Elfstrom Stadium | dnq |
| 1999 | Kane County Cougars | Midw | Central | 137 | 78 | 59 | .569 | -- | 777 | 617 | 160 | Rick Renteria | | 451,145 | 0 | Elfstrom Stadium | Lost in Semi-Finals |
| 1998 | Kane County Cougars | Midw | Central | 140 | 69 | 71 | .493 | 3.0 | 644 | 662 | -18 | Juan Bustabad | | 481,352 | 0 | Elfstrom Stadium | dnq |
| 1997 | Kane County Cougars | Midw | Central | 138 | 70 | 68 | .507 | 5.5 | 667 | 620 | 47 | Lynn Jones | | 436,505 | 0 | Elfstrom Stadium | Lost in Semi-Finals |
| 1996 | Kane County Cougars | Midw | Central | 153 | 65 | 88 | .425 | 22.5 | 580 | 596 | -16 | Lynn Jones | | 436,076 | 0 | Elfstrom Stadium | dnq |
| 1995 | Kane County Cougars | Midw | Central | 138 | 69 | 69 | .500 | 18.5 | 706 | 668 | 38 | Lynn Jones | | 477,550 | 0 | Elfstrom Stadium | Lost in 1st Round |
| 1994 | Kane County Cougars | Midw | Northern | 139 | 71 | 68 | .511 | 18.0 | 705 | 591 | 114 | Lynn Jones | | 417,744 | 0 | Elfstrom Stadium | dnq |
| 1993 | Kane County Cougars | Midw | Northern | 137 | 75 | 62 | .547 | 5.5 | 602 | 560 | 42 | Carlos Tosca | | 354,327 | 0 | Elfstrom Stadium | dnq |
| 1992 | Kane County Cougars | Midw | Northern | 137 | 61 | 76 | .445 | 17.0 | 547 | 607 | -60 | Joel Youngblood | | 323,769 | 0 | Elfstrom Stadium | dnq |
| 1991 | Kane County Cougars | Midw | Northern | 135 | 68 | 67 | .504 | 7.5 | 618 | 565 | 53 | Bob Miscik | | 240,290 | 0 | Elfstrom Stadium | Lost in Semi-Finals |
| 30 record(s) |