[1][2] Hill joined Sheffield United as a youth player on 25 August 2005,[3] but was released at the end of the 2005-06 having never played a first team game for the Blades.
He trialed with Luton Town during the summer of 2006, but was not offered a contract, and eventually signed for Rushden & Diamonds of the Football Conference on 4 January 2007.
Hill moved to the United States in 2010 and was a pre-season trialist with FC Tampa Bay prior to their first competitive season in the USSF Division 2 Pro League.
When his father was hired as the head coach of the club in 2011, Hill returned to the United States, trialed with the team during the 2011 pre-season, and signed a formal contract on 6 April 2011.
Ricky Hill did coach Shane for the Tampa Bay Rowdies in the North American Soccer League before both were let go.