Jack Deaman (or Dearman) played on trial for Norwich in a number of games in the summer of 2011, including the friendlies against Wroxham and Billericay. Previously with Wrexham, he signed for Birmingham on 31st August 2011 despite interest from Norwich, Burnley and Celtic.

He trialled with Port Vale's reserves on 13th March 2013 but joined Chelternham on loan on 28th March 2013 until the end of the 2012/13 season.

Released by Birmingham, he trialled with Torquay United and then Cambridge United in October 2013, playing in a friendly against a West Ham XI.

He subsequently signed for Eastbourne Borough before returning to league football with Cheltenham on 21st July 2014 signing a one year contract. Deaman was transfer-listed by Cheltenham on 4th May 2015 following their relegation to the Conference on 25th April.

He spent the first half of the 2015/16 season on loan to Telford before joining Basingstoke Town. In the summer of 2016, he joined Gloucester City. He was loaned to Salford City in November 2016.