Rocastle played seventeen games of the club's 2005–06 Championship season, before going out on loan to League One side Yeovil Town in late-March. At the end of the season Rocastle's contract at Wednesday was terminated by mutual consent, and he quickly signed for Oldham Athletic. He played 35 league games in 2006–07, helping Oldham to a play-off place, though most of these appearances were as a substitute. In the play-offs they were defeated by eventual promotion winners Blackpool in the semi-finals.