Wessex League Cup, hay 'Sydenhams League Cup' do mục đích tài trợ, là một giải đấu cup địa phương dành cho tất cả các đội bóng ở Wessex League.

Các nhà vô địch Wessex League Cup

• 1986–87 Road Sea Southampton
• 1987–88 East Cowes Victoria Athletic
• 1988–89 AFC Lymington
• 1989–90 A.F.C. Totton
• 1990–91 Thatcham Town
• 1991–92 Thatcham Town
• 1992–93 Gosport Borough
• 1993–94 Wimborne Town
• 1994–95 Thatcham Town
• 1995–96 Downton
• 1996–97 Thatcham Town
• 1997–98 Aerostructures Sports & Social
• 1998–99 Cowes Sports
• 1999–2000 Wimborne Town
• 2000–01 Không tổ chức
• 2001–02 Andover
• 2002–03 A.F.C. Totton
• 2003–04 Winchester City
• 2004–05 Hamworthy United
• 2005–06 A.F.C. Totton
• 2006–07 Lymington Town
• 2007–08 Wimborne Town
• 2008–09 VT
• 2009–10 Bemerton Heath Harlequins
• 2010–11 Bournemouth
• 2011–12 Christchurch
• 2012–13 Alresford Town
• 2013–14 Alresford Town