Chilwell’s first taste of senior football came with Leicester City, having joined their Academy aged 12. He made his full debut in October 2015, before joining Huddersfield Town a month later for a short-term loan in the Championship.
The attacking full-back became a first-team regular at the Foxes the following season and would go on to make 123 appearances for Leicester across a five-year spell, prior to joining Chelsea in August 2020.
During his time at Stamford Bridge, the defender won both the UEFA Champions League and UEFA Super Cup.
Chilwell also made his senior international debut for England in 2018 at the King Power Stadium, during a 1-0 win over Switzerland. He has won 21 caps for the Three Lions to date, scoring his first goal for the team against Andorra in October 2021, and was part of the England squad which reached the Euro 2020 final at Wembley.
Bringing Champions League-winning experience, goalscoring pedigree, and a leadership mentality of fine ilk, he made his debut for Palace in the FA Cup fourth round in February 2025, coming on at half-time in a 2-0 win away at Doncaster. He then made his home debut in the following Premier League game against Everton at Selhurst Park.
Chilwell made 11 appearances during his half-season loan stint in SE25, scoring in his final outing at Selhurst Park against Wolverhampton Wanderers. He departed with an FA Cup winners' medal, the first of his already-decorated career.