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Stephen hails from Berwick Hills in Middlesbrough. He made his U18s debut in 2016/17 and has represented his country up to an including U19s level, scoring a hat-trick against Macedonia in October 2018.

Stephen came off the bench for his first team debut in the Carabao Cup win over Notts County in August 2018 and was also a second-half substitute in the Emirates FA Cup victory at home to Peterborough United the following January. 

At the end of January 2019, he signed a new four-and-a-half year contract with the club and immediately went on loan to MK Dons where he made seven appearances as the Dons secured promotion from League Two.