 Dempsey rejoined Manchester United after the departure of José Mourinho in December 2018 as part of caretaker manager Ole Gunnar Solskjær's coaching staff, taking on the role of a technical coach.In 2019 whilst Manchester United were on their pre-season tour of Australia Dempsey was struck ill and was admitted to hospital.He was subsequently off work for the next couple of months before returning to his role in December 2019.