The 2005–06 Wessex Football League was the 20th season of the Wessex Football League. The league champions for the second time in their history were Winchester City, who were promoted to the Southern League along with runners-up Thatcham Town and third-placed Andover. The extra promotions were because of the pyramid reorganisations that took place in 2006. For sponsorship reasons, the league was known as the Sydenhams Wessex League.