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. It took until 23 November 2013 for Craddock to score his first Portsmouth goal, in a 2–1 loss against Scunthorpe United. However, Craddock struggled in the first team at Portsmouth, due to injury and loss of form that led to being on the substitution bench. In late-November, Craddock suffered a knee injury during the match against Southend United, which is considered as serious.