Timlin began the 2008/2009 season in his preferred central midfield role. However, Maurice Malpas took Timlin out for the visit of Leeds United, and on his return to the squad a week later, he appeared on the left side of midfield. Towards the end of October, when Malpas' defensive-minded approach hadn't appeared to work, Timlin was moved to yet another new position on the left side of the defence to fill the gap of injured Jamie Vincent. Adapting well, Timlin also stood in as captain in the absence of Hasney Aljofree. Maurice Malpas was sacked in November, and Timlin moved back to central midfield under caretaker manager David Byrne.