When the Wessex Football League expanded for the start of the 2004–05 campaign, the club moved to the newly created Division two. The next season saw the club enter the FA Vase for the first time, where they were knocked out in the First Qualification round by Westbury United. The club stayed in the Wessex league a further season, when they finished bottom of the league and were relegated to the Dorset Premier Football League. In 2013–14, Shaftesbury Town continued their Dorset Premier League challenge, starting on 10 August against Wareham Rangers.