Under 16 Cup Winners: Cowrdrys Challenge Cup
1972 Turbary
1973 Northbourne
1974 Longfleet St Marys
1975 Lagland Street YC
1976 Woodlands
1977 Strouden Rangers
1978 Charminster Saints
1979 Wayfarers
1980 No Comp
1981 Charminster Saints
1982 Saints United
1983 Charminster Saints
1984 Branksome United
1985 Iford
1986 Dexter Sports
1987 Flight Colts
1988 Flight Colts
1989 Bisterne United
1990 Greenfields
1991 Park Rangers
1992 Branksome United
1993 B’mth Poppies
1994 Charminster Saints
1995 Grange Athletic
1996 Poole Town Youth
1997 Bournemouth Electric
1998 Charminster Saints
1999 Bournemouth Electric
2000 Bournemouth Electric
2001 Christchurch Youth
2002 Merley Allendale
2003 Bournemouth Electric
2004 B’mth Sports Grange
2005 Branksome United
2006 Branksome United
2007 Branksome United
2008 Redhill Rangers
2009 Redhill Rangers
2010 Redhill Rangers
2011 Branksome United
2012 B’mouth Poppies
2013 Highcliffe Hawks
2014 Branksome United
2015 Poole Town Youth
2016 Boscombe Albion
2017 Bournemouth Electric
2018 Lymington Sprites
2019 Brockenhurst Youth
2020 – No Competition
2022 – Boscombe Albion Youth
2023 – Highcliffe Hawks