Healy won his second league title as a manager during the 2018–19 campaign, with Linfield finishing seven points ahead of second-placed Ballymena United and Healy also being named as Manager of the Year. He also added the League Cup to his collection, as Linfield defeated Ballymena United 1–0 in the final. Linfield also reached the 2019 County Antrim Shield final, losing out 4–3 to Crusaders. He stated that he was looking t strengthen the first-team in the summer, saying that "we're not just going to be bringing in players for the sake of making up the numbers, we're going to be bringing in players who will be challenging for a starting berth".