Hills started his career at Wimbledon at the age of nine, spending five years at the club's academy before briefly joining Arsenal.
[3] In the summer of 2005, Hills was invited to train at Crystal Palace's academy, and subsequently signed a two-year scholarship deal at the club.
[5] Two months later, Hills appeared in the club's 2–1 away victory at Queens Park Rangers,[6] and would go on to feature regularly throughout December 2007 and January 2008 during a spell that witnessed Palace rise up the Championship table.
[17] He made his debut for Oldham in a 2–0 home loss to Leeds United in the FA Cup,[18] and went on to make four appearances during the loan spell.
[16] In his final game for Oldham, Hills received the first red card of his career, for two bookable offences, in a 3–0 defeat to Walsall.
[21][22][23] In March 2012, Hills was loaned out to promotion chasing League Two side Southend United for the remainder of the season, in order to regain match fitness.
[21] In July 2012, Hills joined League One side Stevenage on trial, playing in the club's pre-season friendly draw with Boreham Wood.
[32][33] The first three months of Hills' Stevenage career were disrupted by injury, eventually making his first-team debut in a 4–1 away defeat to Sheffield United in November 2012.
[34] Further injuries meant Hills appeared sporadically during the second half of the season, impressing in Stevenage's 4–0 victory over Sheffield United on 16 March 2013.
[36] Struggling to break into the first team, Stevenage and Hills mutually agreed to the termination of his contract, and he dropped down three divisions to join Whitehawk in the Conference South.