 On 26 April 2010 it was announced that Bailey was in the 2009–10 PFA team of the year alongside teammate Frazer Richardson.Bailey captained Charlton to a semi-final playoff defeat against Swindon Town, the semi-final went to penalties and it was Bailey who missed the decisive spot kick for Charlton to send Swindon through to the final.It was to be his last kick as a Charlton player.