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Chelsea
Cumming joined Chelsea at the age of eight, enrolling in the club's development programme. He progressed through the various age groups at Chelsea and became the under-17 team's first-choice goalkeeper at the start of the 2017–18 season. That season, he played twice for the club's under-21 team in the EFL Trophy, making his debut in a 2–2 draw away to Plymouth Argyle on 15 August 2017. Cumming also featured regularly for the club's under-19 team that season; saving three penalties in the club's UEFA Youth League semi-final penalty shoot-out victory over Porto on 20 April 2018. He signed a professional contract with Chelsea in November 2018, keeping him contracted to the club until the end of the 2020–21 season. Cumming played eleven times for the under-21 team in EFL Trophy matches over the next three seasons.Cumming was named on the substitute's bench for Chelsea's 4–1 UEFA Europa League Final victory over Arsenal in Baku on 29 May 2019.


