| Year | City Champs | Manager | WSLL President |
| 1970 | | | Tom Karch |
| 1971 | Fairfield Pease's | | Tom Karch |
| 1972 | Fairfield Minnielli | | Tom Karch |
| 1973 | | | Tom Karch |
| 1974 | Fairfield Landmark | Ralph Smith | Lee Purdy |
| 1975 | Fairfield Landmark | Ralph Smith | Lee Purdy |
| 1976 | Fairfield Landmark | Ralph Smith | Lee Purdy |
| 1977 | Fairfield Landmark | Ralph Smith | Lee Purdy |
| 1978 | Northend Aamco Transmission | | Lee Purdy |
| 1979 | Northend Columbia Oil | | Lee Purdy |
| 1980 | Fairfield Home Federal | | Lee Purdy |
| 1981 | Northend Columbia Oil | | Don Anderson |
| 1982 | Northend Modern Food | | Don Anderson |
| 1983 | Northend Aamco Transmission | | Gerald Lanich |
| 1984 | Northend Washington Lodge | | Bill Arnold |
| 1985 | Fairfield Millillo's Pizza | | Bill Arnold |
| 1986 | Kiwanis Cubs | Steve Boyer | Bill Arnold |
| 1987 | Davis Garage Mets | Grady Morris | Mark Henry |
| 1988 | Harts Roto Rooter White Sox | Ray Nichting | Mark Henry |
| 1989 | May's Heating Pirates | Tom Vessely | Mark Henry |
| 1990 | Society Bank Athletics | Bob Bachman | Grady Morris |
| 1991 | Davis Garage Mets | Mark Henry | Bill Arnold |
| 1992 | Fairfield Jungle Jims | | Bill Arnold |
| 1993 | Hart Paving/Sealing White Sox | Ray Nichting | Bill Arnold |
| 1994 | Wilks Insurance Yankees | Darrel Grissom | Bill Arnold |
| 1995 | Hart Paving/Sealing White Sox | Ray Nichting | Larry Creech |
| 1996 | Dully' Drive Thru Expos | Rusty Couch | Larry Creech |
| 1997 | West Side Cleaners Cardinals | Tom Weiser | Larry Creech |
| 1998 | Ohio Casualty Red Sox | Ken Coomer | Larry Creech |
| 1999 | Wheeler Insurance Indians | Jerry Margerum | Larry Creech |
| 2000 | Kiwanis Cubs | Dale Mahon | Aggie Cole |
| 2001 | Robinson Fence Mets | Nick Fries | Dave Davidson |
| 2002 | Ohio Casualty Red Sox | Ken Coomer | Mike Benigar |
| 2003 | May's Heating Pirates | Steve Sams | Mike Benigar |
| 2004 | Wilks Insurance Dodgers | Cliff Carter | Mike Benigar |
| 2005 | Ohio Casualty Red Sox | Ken Coomer | Steve Monnin |
| 2006 | Wilks Insurance Dodgers | Tim Reed | Steve Monnin |
| 2007 | May's Heating Pirates | Tim Nichting | Jerry Lauer |
| 2008 | Lewis Collision Center Reds | Mike Robbins | Jerry Lauer |
| 2009 | Walts Barbeque White Sox | Tim Robinson | Jim Sheffstall |
| 2010 | Wilks Insurance Dodgers | Tim Nichting | Jerry Lauer |
| 2011 | May's Heating Pirates | Jon Brandburg | Dave Hughes |
| 2012 | Jeff Pohlman Red Sox | Ken Coomer | Steve Monnin |
| 2013 | Berkley Square Orioles | Craig Mills | Traci Hamilton |
| 2014 | May's Heating Pirates | Matt Kirkendall | Traci Hamilton |
| 2015 | May's Heating Pirates | Matt Kirkendall | Traci Hamilton |
| 2016 | Lewis Collision Center Reds | Tracy Avery | Traci Hamilton |
| 2017 | Lewis Collision Center Reds | Tracy Avery | Becky Couch |
| 2018 | Robert Brown Construction Cubs | Mark Nichting | Becky Couch |
| 2019 | Rib City Cubs | Mark Nichting | Josh Davidson |
| 2020 | Lewis Collision Center Reds | Danny Adams | Josh Davidson |
| 2021 | Chick'nCone Red Sox | Kenny Coomer | Josh Davidson |
| 2022 | Chick'nCone Red Sox | Kenny Coomer | Josh Davidson |
| 2023 | Auto Express Cubs | Tim Nichting | Josh Davidson |