| Year | Division | Gender | Champion | Runner-up | Score |
|---|---|---|---|---|---|
| 1990 | U16 | Boys | Tosa Arsenal | Brookfield | |
| 1991 | |||||
| 1992 | |||||
| 1993 | |||||
| 1994 | |||||
| 1995 | |||||
| 1996 | U16 | Boys | MK Nationals | ||
| 1997 | U16 | Boys | Mequon United FC | ||
| 1998 | U16 | Boys | Madison UA Wave | ||
| 1999 | U16 | Boys | MK Nationals | ||
| 2000 | U16 | Boys | Elmbrook United | ||
| 2001 | U16 | Boys | FC Milwaukee Nationals | ||
| 2002 | U16 | Boys | Yahara-56ers Blue | Parkland SC | 2-1 (OT) |
| 2003 | U16 | Boys | FC Milwaukee Nationals | Mequon Red | 3-1 |
| 2004 | U16 | Boys | Yahara Blue | ||
| 2005 | U16 | Boys | Madison 56ers | Yahara-Middleton | |
| 2006 | U16 | Boys | FC Milwaukee Blue | ||
| 2007 | U16 | Boys | FC Milwaukee Blue | ||
| 2008 | U16 | Boys | Elm Grove Academy | ||
| 2009 | U16 | Boys | Croatian Eagles | ||
| 2010 | U16 | Boys | Elm Grove Premier | ||
| 2011 | U16 | Boys | SC Waukesha Pumas | ||
| 2012 | U16 | Boys | Everton 95/96 | ||
| 2013 | U16 | Boys | United FC | ||
| 2014 | U16 | Boys | SC Waukesha | Croatian Eagles SC | 2-1 |
| 2015 | U16 | Boys | FC Wisconsin | North Shore United | 2-1 |
| 2016 | U16 | Boys | SC Waukesha | Elm Grove SC | 2-1 |
| 2017 | U16 | Boys | Red Star SC | North Shore United | 3-0 |
| 2018 | U16 | Boys | Madison 56ers SC | SC Waukesha | 1-0 |
| 2019 | U16 | Boys | Milwaukee Bavarians | SC Waukesha | 2-0 |
| 2020 | U16 | Boys | No tournament (COVID-19 pandemic) | ||
| 2021 | 16U | Boys | Madison 56ers Red | SC Wave Juniors | 2-1 |
| 2022 | 16U | Boys | SC Wave Juniors | Bavarian United Blue | 2-1 |
| 2023 | 16U | Boys | Rush Wisconsin 2007 | Croatian Eagles 2007 Red | 3-3 (4-3 pen) |