He signed for League One club Gillingham on a one-month loan on 15 October 2009.[4] He made his debut on 17 October 2009, in a 2–0 away defeat against Milton Keynes Dons.[5] In November 2009, his loan with Gillingham was extended for a further month,[6] and in December extended again for another month.[7] Fry suffered a knee injury in Gillingham's away match against Exeter City on 28 December 2009, ruling him out of action for six weeks.[citation needed] On 7 January 2010, he returned to West Ham.[8]
On 25 March 2010, he signed for League One club Charlton Athletic until the end of the season,[9] but returned to West Ham without having played for Charlton due to a persisting knee problem suffered earlier in the year.[10] On 5 August 2010, Fry again joined Charlton on loan, this time until January 2011.[11] On 28 August 2010, Fry made his first appearance for Charlton and scored his first goal, in a 3–1 away defeat to Huddersfield Town.[12] On 22 March 2011, Fry returned to West Ham having made 32 appearances, scoring one goal, for Charlton.[13]
Fry had his contract cancelled by mutual consent with West Ham on 2 February 2012 allowing him to seek first-team football on a regular basis.[14]
Bradford City
On 10 February 2012, Fry joined League Two club Bradford City on a free transfer.[15] He made his debut in a 1–1 draw at home to Port Vale on 14 February 2012, in which he played 79 minutes before being substituted.[16]
Fry signed for newly relegated National League club York City on 16 June 2016 on a two-year contract.[20] His contract with York was cancelled by mutual consent on 26 September 2017 to retire from full-time football on medical advice.[21]