 In March 2008 he collected a Scottish League Cup runners-up medal despite being an unused substitute in the final.However, on 15 May 2010, he was then a part of the Dundee United team who defeated Ross County 3–0 to lift the Scottish Cup at Hampden Park.Not long after the beginning of the 2012–13 season Dillon signed a contract extension that would keep him at the club until May 2015.