In April 2021 it was announced that he would move to England for the first time to join the Fleetwood Town International Football Academy at the end of the year.
[1] His performances there led to a loan to Kendal Town being announced,[2][3] but registration issues caused the move to collapse.
[4] After Anchorsholme folded at the end of the season, Jessop returned to Gibraltar to join FCB Magpies.
[6] He made his first start a month later in the next round of the competition, as the Spireites fell to a 2–0 defeat to Welling United.
[11] He would become a regular fixture in the team 2 years later during the 2025 UEFA European Under-21 Championship qualification campaign, notably registering assists for Dylan Borge in the 3–1 defeat to Moldova on 15 June 2023[12] and for Tayler Carrington in the 2–1 victory against the same opponents on 21 November 2023.