On 7 April 2021, Chilwell scored his first UEFA Champions League goal in a 2–0 away win over Porto in the first-leg of the quarter-final tie. On 16 May, Chilwell scored against his former club Leicester City in the FA Cup Final in the 88th minute, only for it to be disallowed by VAR, as Leicester went on to win 1–0 and their first ever FA Cup. On 29 May, Chilwell won his first-ever trophy after Chelsea defeated Manchester City 1–0 in the 2021 UEFA Champions League Final in Porto.