Jamie was a promising young Leeds United midfielder when Gary McAllister brought him to Coventry on loan in November 2002. He had made two substitute appearances in the Premiership for Leeds and it was felt a spell in the lower division would be good experience for him. The young Aussie made two starts for the Sky Blues, both defeats, against Ipswich and Preston, before suffering a medial injury.

He returned to Elland Road and made 13 appearances over three seasons before joining Chesterfield in 2005 after loans at Swindon and Peterborough. His stay at Chesterfield was brief and he left after eight games. After a short spell at Aarhus in Denmark he returned to Australia and played two seasons for A League side Central Coast Mariners.