On 5 February 2013, in a match against Leyton Orient, Timlin suffered a broken leg and was out of action for 8–9 months. He then missed the second leg of that game, the JPT Area Final, and the subsequent Wembley final. It was hoped that he would be back for the start of the next season 2013–14. Despite the injury, Timlin was offered, and signed, a new 2-year contract. He made his return from injury after appearing on the bench for three matches, when he came on as a substitute in the 83rd minute, in a 2–1 loss against Chesterfield on 24 August 2013. At the end of the 2014–15 season he played for Southend in the League Two play-off final against Wycombe Wanderers. Southend won in a penalty shoot-out and were promoted to League One.