Jack Simpson

Weymouth-born, Jack Simpson came through the youth ranks at AFC Bournemouth, joining the club at the age of 12. He worked his way to the first team and, with a loan spell at AFC Totton along the way, went on to make 35 appearances for Bournemouth between 2015 and 2021 before his contract expired.

A free transfer took him to Rangers in January 2021, with Bournemouth holding a sell-on clause on any future move. He spent under two years in Glasgow before joining Cardiff City in August 2022 for an undisclosed fee, going on to make 20 league appearances for the Welsh club. That spell ended abruptly: his contract was terminated by mutual consent in August 2023 after an FA misconduct charge tied to a racist slur during Cardiff's pre-season tour that summer.

Simpson spent six months as a free agent before Leyton Orient signed him on a free transfer at the end of February 2024. He was initially tied to a short-term deal through the end of that season, but the club took up the option to extend him into the 2024–25 campaign, and he signed a further one-year extension in June 2025, keeping him at Brisbane Road until the summer of 2026. He has made 57 league appearances for Orient.