Gregan returned to Darlington on 4 June 2012 as a player-coach, as part of new manager Martin Gray's backroom staff. He was appointed as joint manager of Darlington, alongside Brian Atkinson, on 1 October 2017 for the rest of the 2017–18 season after Gray left for the club's National League North rivals York City. However, the two left the club four days later without having taken charge of a match. With Atkinson also being a director of the Martin Gray Football Academy (MGFA), Football Association rules meant he was unable to hold the Darlington managerial position as the academy's owner was in charge at another club. Gregan turned down the offer of a six-month contract to take over as manager on his own, as he would have had to relinquish his own role the MGFA.
