 In May 2013, having been released by Sunderland, Maddison signed permanently for Crawley Town on a one-year contract, but failed to make an appearance for the Sussex club before being released at the end of the 2013–14 season.Maddison then joined the development side of Premier League club Leicester City.In March 2015, Maddison joined National League North side Leamington on loan until the end of the 2014–15 season.