Brittain captained Ross County through victories in The Scottish Cup against SPL sides Hibs and Celtic. The famous 2–0 victory over Celtic at Hampden Park in the semi-final earned Ross County a place in the 2010 Scottish Cup Final, the club's first ever major final, which County eventually lost 3–0 to Dundee United. Brittain dedicated the win against Celtic to his late friend Graham Heggie. During the 2009–10 season, Brittain signed a new contract with the club. In the 2010–11 season, Brittain would be involved in leading Ross County to a 2–0 win against Queen of the South in the final of the Scottish Challenge Cup.