Born in Sheffield, South Yorkshire, Wilkinson is the son of former player and manager Howard Wilkinson. He played with the youth teams of Sheffield Wednesday, Sheffield United and Derby County, becoming a scholar with the latter in May 2003. He joined Hull City in January 2005, where he completed his scholarship. He signed a two-year professional contract with Hull in the summer of 2006. He joined Conference North club Harrogate Town on 9 December 2006 on a one-month loan, where he made five appearances before returning to Hull in January 2007.
He joined Conference Premier club York City on 10 June 2008 on a two-year contract. His debut came in a 1–0 away win against Crawley Town on 9 August 2008. He scored his first goal in a 3–1 defeat away to Wrexham on 7 October 2008.
wilkinson signed for newly relegated Conference Premier club Chester City on 9 July 2009. Wilkinson scored in the first minute of his debut against Cambridge United on 15 August 2009, but Chester lost 4–2. He made 28 appearances for Chester in 2009–10, although these were expunged from the records after Chester were expelled from the Football Conference in March 2010. He left the club following their liquidation on 10 March 2010 and in April went on trial with League Two club Bradford City, playing in reserve-team matches against Newcastle United and Leeds United.
Wilkinson signed for Conference Premier club Tamworth on 26 August 2010 following a trial. His first goal came in a 1–0 away win over Mansfield Town, with a shot into the bottom corner from six yards from Danny Thomas' pass on 30 minutes. Wilkinson scored a goal against York in a 2–1 away win on 16 April 2011 to help Tamworth fight relegation.
Wilkinson signed for Conference North club Boston United on 30 July 2011 after a trial, having been set to follow former Tamworth players Aaron Mitchell and Jason Bradley to Eastwood Town. He found himself out of the team early in 2011–12 because of a knee injury but later established himself at right back due to a shortage in that position. He left Boston on 7 November 2011 after making 10 appearances for the club.
By November 2013, Wilkinson had taken on the position of youth development phase coach at Sheffield Wednesday.
