Stephenson started his career in Sunderland's academy, before signing for Liverpool in September 2018.[2][3]
Stephenson captained Liverpool's under-18 team for the 2020–21 season, going on to also captain the under-21 side, becoming a regular with them in the following season.[3]
During his time in Liverpool's academy, Stephenson was versatile, playing at both centre-back and right-back in addition to his natural midfield role.[3]
Liverpool
Stephenson signed his first professional contract in September 2020,[4] with his deal being extended in February 2022.[5]
Loan to Barrow
On 1 September 2023, Stephenson joined EFL League Two club Barrow on a season-long loan.[6][7] On 5 September, he made his professional debut in an EFL Trophy fixture against Blackpool.[8] He later made his professional league debut on 30 September against Doncaster Rovers, coming on as a substitute for Tyrell Warren in the 62nd minute.[9] On 14 October 2023, Stephenson made his full league debut at right-wing-back as Barrow faced Milton Keynes Dons, being replaced after 46 minutes.[10]
During his time at Barrow, Stephenson was mainly deployed on the right of a back-five, with his hard-working and tough tackling style making him popular amongst fans.[11] He became a regular in a Barrow team that narrowly missed-out on the League Two 2024 English Football League play-offs by a single point, one of their best league finishes in a 122-year history.[12]