On 5 February 2004, in the semi-final of that season's Scottish League Cup at Hampden Park versus Rangers, Dobbie scored the equalising goal in the 79th minute. The match ended 1–1 after extra time and Hibs won 4–3 on penalties. Despite this, Dobbie failed to win a regular place in the Hibernian first-team as Garry O'Connor and Derek Riordan were preferred to him. Dobbie was a 70th-minute substitute in the 2004 Scottish League Cup Final defeat by Livingston; Hibernian lost 2–0.