 Baillie made just two appearances in Tony Mowbray's time as manager and wasn't picked after a 4–4 home draw against Dundee in September 2004.He had a brief loan spell at Ayr United in January 2006, but did not play a first-team game for Hibernian in over two and a half years.Baillie was the victim of a catalogue of injury problems, which forced him to retire from senior football at the end of the 2006–07 season, aged just 21.