Team Handicap KO Cup Winners 1993 – Present
| Year | Winner |
|---|---|
| 1993 | Southbourne |
| 1994 | Southbourne A |
| 1995 | Weymouth A |
| 1996 | New Milton |
| 1997 | Oakdale A |
| 1998 | Weymouth A |
| 1999 | New Milton A |
| 2000 | Wimborne B |
| 2001 | Kinson |
| 2002 | Kinson |
| 2003 | Weymouth |
| 2004 | Wimborne |
| 2005 | Wimborne A |
| 2006 | Dorchester |
| 2007 | Wimborne B |
| 2008 | Southbourne |
| 2009 | Weymouth |
| 2010 | Wimborne |
| 2011 | Wimborne B |
| 2012 | Wimborne |
| 2013 | Bridport |
| 2014 | Wimborne |
| 2015 | Poole |
| 2016 | Highcliffe |
| 2017 | Poole |
| 2018 | Poole |
| 2019 | Highcliffe |
| 2020 | Not held (COVID) |
| 2021 | Highcliffe |
| 2022 | Southbourne |
| 2023 | Poole |
| 2024 | Highcliffe Fischers |
| 2025 | Southbourne Sharks |