Martin came up through the youth ranks at Coventry City before making the switch to Whaddon Road in July 1999 joining on to make 226 first team appearances for the Robins, netting 43 goals. He played against the Reds in both meetings during the 2002/2003 League One campaign. Martin left Cheltenham in the summer to join up with Championship side Watford but thing did not work out at Vicarage Road and the winger switched to South Yorkshire.

Although he struggled a little to start with, Martin soon settled in at Oakwell and was in fine form as the Reds won promotion back to the Championship. He contributed eight goals along the way and his scintillating wing play entertained the Reds faithful throughout 2005/2006.

Martin enjoyed a spectacular campaign in the Championship during 2006/2007 as his impressed throughout the season on the right wing. He bagged six goals in 44 games in all competitions.

Martin enjoyed another successful season in 2007/2008 as he put in a fine shift for the Reds to secure Championship security and chipped in with some important goals along the way. He was outstanding against Liverpool and Chelsea in the FA Cup, picking up two assists to help the Reds into the Semi Finals.