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Sheaf joined League One side Doncaster Rovers on loan on 12 July 2019, joining the League One side for six months. The deal was extended until the end of the 2019–20 season on 7 January 2020.

Sheaf joined League Two side Stevenage on loan on 26 January 2018, joining the Hertfordshire club on a deal until the end of the 2017–18 season.

In October 2015, Sheaf was invited to train with the first team, and days later he was an unused substitute in the club's 3–0 defeat against Sheffield Wednesday. He stated that, although the result was not satisfactory, the experience of being involved in the first-team was good for him as he got to "see how things are done". He made his first-team debut for Arsenal on 19 October 2017, coming on as an 89th-minute substitute for Francis Coquelin in a 1–0 victory over Red Star Belgrade in the UEFA Europa League.

Sheaf started his youth career with the reserves of West Ham United at the age of 13, before joining the Arsenal youth setup on 2 July 2014. He earned the praise of senior team manager Arsène Wenger who said that Sheaf was "always ahead of the game". He scored his first goal for the Arsenal U19 in a 3–2 victory over Greek club Olympiacos on 29 September 2015, where he found the net in the 41st minute from the penalty spot.

Sheaf debuted for England under-16 team in the Victory Shield. As of July 2014, he has played twice for the under-16 national team. He was part of the England U18's which played a couple of friendlies against the Netherlands in September 2015. They won 2–0 in the first game which Sheaf scored a penalty and drew the second game 0–0.

Benjamin David Sheaf (born 5 February 1998) is an English footballer who plays as a midfielder for club Doncaster Rovers on loan from Arsenal. He has represented England at youth level.