 Gwynne was born in Hereford and joined the Hereford United youth team, which is associated with the Pershore College football academy at Holme Lacy.He was an unused substitute for several first team matches during the 2004-05 season and started the Conference League Cup match against Northwich Victoria.His league debut came in the 2005-06 season when he featured as a substitute in the dying minutes of the televised match at home to Stevenage Borough.