| Year | Division | Gender | Champion | Runner-up | Score |
|---|---|---|---|---|---|
| 1996 | U15 | Boys | MK Nationals | ||
| 1997 | U15 | Boys | Mequon United FC | ||
| 1998 | U15 | Boys | MK Nationals | ||
| 1999 | U15 | Boys | Parkland SC | ||
| 2000 | U15 | Boys | MK Nationals | ||
| 2001 | U15 | Boys | Parkland SC | ||
| 2002 | U15 | Boys | FC Milwaukee Nationals | Mequon United | 2-0 |
| 2003 | U15 | Boys | Brookfield SA Red | FC Milwaukee Nationals | 2-1 |
| 2004 | U15 | Boys | Elm Grove Premier | ||
| 2005 | U15 | Boys | FC Milwaukee | PVYSA Neenah United | |
| 2006 | U15 | Boys | Croatian Eagles | ||
| 2007 | U15 | Boys | FC Milwaukee Blue | ||
| 2008 | U15 | Boys | Madison 56ers Red | ||
| 2009 | U15 | Boys | Elm Grove Premier | ||
| 2010 | U15 | Boys | Madison FC Gold | ||
| 2011 | U15 | Boys | Milwaukee Bavarians | ||
| 2012 | U15 | Boys | United FC | ||
| 2013 | U15 | Boys | North Shore Blue | ||
| 2014 | U15 | Boys | Rush Wisconsin | Milwaukee Bavarians | 1-0 |
| 2015 | U15 | Boys | Madison FC | Milwaukee Bavarian | 2-1 |
| 2016 | U15 | Boys | Milwaukee Bavarians | SC Waukesha | 2-1 |
| 2017 | U15 | Boys | SC Waukesha | Madison 56ers SC | 2-0 |
| 2018 | U15 | Boys | SC Waukesha | United Soccer of Allouez | 3-0 |
| 2019 | U15 | Boys | SC Waukesha | Rush Wisconsin | 2-1 |
| 2020 | U15 | Boys | No tournament (COVID-19 pandemic) | ||
| 2021 | 15U | Boys | SC Wave Juniors | Bavarian SC Blue | 3-2 |
| 2022 | 15U | Boys | Madison 56ers Red | Croatian Eagles Red | 2-0 |
| 2023 | 15U | Boys | SC Wave Cadence 08 | SC Wave Juniors 08 | 1-0 |