In 2009, Hylton was in the final of Sky1's TV talent showWayne Rooney's Street Striker. Preceding his release from Birmingham City, Hylton had spells with non-league sides Continental Star and Redditch United. On 22 December 2014, Hylton was invited to play in a professional development game for his former club; Birmingham City by manager Gary Rowett against Manchester City. Hylton scored one goal and had a hand in the other two as he helped the development team to a 3–2 victory.
On 3 January 2015 it was reported by Swindon Advertiser that Redditch United started to consider a FA complaint over Swindon's approach to their frontman. The paper stated that Redditch claimed Swindon had broken the 7 day approach until they were allowed to sign the player. On 7 January 2015, Hylton signed for Swindon Town on a -year contract with the club despite Redditch's complaint to the FA over their "illegal" approach. On 12 January 2015, Hylton made his first appearance for Swindon coming on as an 87th-minute substitute for Andy Williams in a 3–0 win against Coventry City at the Ricoh Arena. On 11 April 2015, he went on to score his first goal and the winning goal against Peterborough United. On 4 October 2016, Hylton joined National League side Guiseleyon loan until January 2017. On the same day, Hylton scored on his Guiseley debut in their 6–1 home victory over York City, netting the host's fifth in the 55th minute before being replaced by Michael Rankine in the closing stages of the game. Hylton went onto feature in four more games for Guiseley before being recalled by parent club; Swindon in December 2016. In February 2017, Hylton was fined by Swindon Town after he walked out on his side prior to their game against Northampton Town. After having being told he wasn't involved with in the matchday squad by manager Luke Williams.
On 13 July 2017, after a successful trial period, Hylton joined National League side Solihull Moors. After struggling with a long-term injury, Hylton made his Solihull debut in their FA Cup fourth qualifying round tie against Ossett Town in October 2017, in which he featured for the full 90 minutes in the 1–1 draw. On 24 October 2017, Hylton scored his first goal for Solihull during their 2–1 away victory over Eastleigh, netting the game's opener in the 4th minute. On 10 May 2019, it was announced that Hylton was to leave The Moors following the conclusion of his contract.
Motherwell
On 29 May 2019, Motherwell completed the signing of Hylton on a free transfer, following the expiry of his Solihull Moors contract, becoming the club's fifth signing of the window. On 13 July 2019, Hylton made his competitive debut for Motherwell in a 3–0 win away to Queen of the South.
