 Dimaio made two further appearances for the Blades before the end of the season, which was enough to see him awarded the club's annual 'Young Player of the Year' award.Dimaio signed for League One side Chesterfield on 1 February 2016, on a contract until the end of the season, having been released by Sheffield United on the same day as he signed for Chesterfield.He scored his first goal for Chesterfield in a 3–1 win against Crewe Alexandra on 20 February 2016.