 Upon joining the club, Craddock was given number 10 shirt for the new season after Yassin Moutaouakil switched to number two shirt.Craddock made his Portsmouth debut, in the opening game of the season, where he played 21 minutes, in a 4–1 home defeat to his former club, Oxford United on 3 August 2013.In the first round of the Johnstone Trophy, Craddock converted the first penalty in the shoot-out, in a 5–3 win over Torquay United after the game went throughout 120 minutes, in a 0–0 draw.