Cresswell returned to York as a commercial, academy and community development consultant in April 2014, having previously intended to pursue a career in coaching. He took on the position of Head of Football Operations, before being appointed as first-team coach to manager Russ Wilcox in March 2015. In May 2015, Cresswell resumed his role as Head of Football Operations, while continuing to coach the first team. He took over as caretaker manager on 26 October 2015 after Wilcox's dismissal, and was assisted by youth team coach Jonathan Greening and goalkeeping coach Andy Leaning. He was in charge for the 1–0 away defeat to Crawley Town on 31 October 2015, before ceasing his caretaker duties upon the appointment of Jackie McNamara as manager on 4 November. Cresswell left York by mutual consent on 16 December 2015.