| Year | Division | Gender | Champion | Runner-up | Score |
|---|---|---|---|---|---|
| 1996 | U14 | Boys | MK Nationals | ||
| 1997 | U14 | Boys | Bavarian SC | ||
| 1998 | U14 | Boys | MK Nationals | ||
| 1999 | U14 | Boys | MK Nationals | ||
| 2000 | U14 | Boys | MK New Berlin Thunder | ||
| 2001 | U14 | Boys | FC Milwaukee Nationals | ||
| 2002 | U14 | Boys | FC Milwaukee Nationals | Brookfield SA Mustangs | 1-0 (OT) |
| 2003 | U14 | Boys | Madison 56ers Red | Mequon SC Red | 2-0 |
| 2004 | U14 | Boys | Polonia SC | ||
| 2005 | U14 | Boys | Yahara-Middleton Blue | FC Milwaukee | |
| 2006 | U14 | Boys | FC Milwaukee Blue | ||
| 2007 | U14 | Boys | Mequon Red | ||
| 2008 | U14 | Boys | FC Milwaukee Blue | ||
| 2009 | U14 | Boys | FC Magic | ||
| 2010 | U14 | Boys | Bavarian Juniors Blue | ||
| 2011 | U14 | Boys | United FC | ||
| 2012 | U14 | Boys | North Shore United | ||
| 2013 | U14 | Boys | United FC | ||
| 2014 | U14 | Boys | Milwaukee Bavarians | Madison FC | 1-0 |
| 2015 | U14 | Boys | ACE North | Appleton SC | 3-2 |
| 2016 | U14 | Boys | SC Waukesha | FC Wisconsin North | 3-1 |
| 2017 | U14 | Boys | FC Wisconsin Nationals | Milwaukee Bavarians | 4-3 |
| 2018 | U14 | Boys | United Soccer of Allouez | Rush Wisconsin | 2-0 |
| 2019 | U14 | Boys | Madison 56ers SC | SC Waukesha | 2-0 |
| 2020 | U14 | Boys | No tournament (COVID-19 pandemic) | ||
| 2021 | 14U | Boys | Madison 56ers Red | Rush Wisconsin | 3-0 |
| 2022 | 14U | Boys | Madison 56ers Red | Croatian Eagles Red | 1-0 |
| 2023 | 14U | Boys | Madison 56ers 2009 Red | Rush Wisconsin 2009 | 1-0 |