| Year | Division | Gender | Champion | Runner-up | Score |
|---|---|---|---|---|---|
| 1992 | U18 | Boys | Mequon United | MK Nationals | |
| 1993 | U18 | Boys | |||
| 1994 | U18 | Boys | |||
| 1995 | U18 | Boys | |||
| 1996 | U18 | Boys | Elm Grove Rampage | ||
| 1997 | U18 | Boys | MK Nationals | ||
| 1998 | U18 | Boys | MK Nationals | ||
| 1999 | U18 | Boys | MK Nationals | ||
| 2000 | U18 | Boys | Brookfield Classic | ||
| 2001 | U18 | Boys | FC Milwaukee Nationals | ||
| 2002 | U18 | Boys | Brookfield Arsenal | DePere Select | 4-0 |
| 2003 | U18 | Boys | Brookfield Lightning | Milwaukee Simba | 2-0 |
| 2004 | U18 | Boys | MK New Berlin Titans | ||
| 2005 | U18 | Boys | FC Milwaukee Nationals | Madison 56ers Red | |
| 2006 | U18 | Boys | FC Milwaukee | ||
| 2007 | U18 | Boys | Madison 56ers Red | ||
| 2008 | U18 | Boys | FC Milwaukee Blue | ||
| 2009 | U18 | Boys | Croatian Eagles | ||
| 2010 | U18 | Boys | Elm Grove Premier | ||
| 2011 | U18 | Boys | Elm Grove | ||
| 2012 | U18 | Boys | Elm Grove Blues | ||
| 2013 | U18 | Boys | Madison 56ers | FC Green Bay Orange | 5-0 |
| 2014 | U18 | Boys | Milwaukee Bavarians | FC Wisconsin | 2-1 |
| 2015 | U18 | Boys | Milwaukee Bavarian | Elm Grove SC | 1-0 |
| 2016 | U18 | Boys | Milwaukee Bavarians | Croatian Eagles SC | 4-0 |
| 2017 | U18 | Boys | Elm Grove SC | Madison 56ers SC | 2-1 |
| 2018 | U18 | Boys | SC Waukesha | Milwaukee Bavarians | 1-0 |
| 2019 | U18 | Boys | Milwaukee Bavarians | Madison 56ers SC | 4-1 |
| 2020 | U18 | Boys | No tournament (COVID-19 pandemic) | ||
| 2021 | 18U | Boys | Bavarian SC Blue | SC Wave Juniors | 3-1 (AET) |
| 2022 | 18U | Boys | SC Wave Juniors | Bavarian United Rosenthal | 6-2 |
| 2023 | 18U | Boys | Madison 56ers 05 Bruner | Elmbrook United Elite | 4-1 |