Harry is an English left back who progressed through the academy at Norwich City where he won the 2013 FA Youth Cup before signing his first professional contract. In August 2015 he made his senior debut for the club away at Rotherham United aged 20. On 12 June 2018 Harry signed for Lincoln City playing every game in the side that guided Lincoln to League One promotion. He also won a place in the PFA League Two team of the year. Harry signed for Huddersfield Town on 17th January 2020 for an undisclosed fee.
Harry is eligible to play for both England and Italy but received his first international call up for England in February 2013 making his debut against Belgium. The following year Harry was with the U19 side in Slovenia for the UEFA Qualifying Tournament where they finished as group winners. In 2015 he was with the England U20 squad for the first time including being involved in the Mercedes Benz Cup Tournament.