At international level, Chilwell made his debut for England in 2018. He was a member of the England squad that finished as runners-up atUEFA Euro 2020.
After featuring for the club in pre-season under new managerClaudio Ranieri, Chilwell was given the number 30 shirt ahead of the2015–16 season.[9] On 27 October 2015, in the club'sLeague Cup match againstHull City, he made his first-team debut. Chilwell played the entire match as Leicester lost 5–4 in apenalty shootout following a 1–1 draw after extra time.[10]
On 19 November 2015, Chilwell joinedChampionship clubHuddersfield Town on aloan until 3 January 2016.[11] He made his debut nine days later in a 2–0 home loss toMiddlesbrough.[12] Despite only spending six weeks at the West Yorkshire club, Chilwell would later describe his spell as "a big part of [his] growth in [his] career"[13] and credited Huddersfield managerDavid Wagner with aiding his development as an attacking full back.[14]
In January 2016, Chilwell was recalled from his loan by Leicester City.[15] On 10 January, he started at left-back and played the full 90 minutes of a 2–2 draw away atTottenham Hotspur in the third round of theFA Cup. Ten days later, he made his first appearance atKing Power Stadium as Leicester were beaten 2–0 by Tottenham in the replay.[16] He was described in the BBC's match report as "Leicester's best player" and "exceptional as an attacking full-back".[17]
On 28 July 2016, Chilwell signed a new contract with Leicester until June 2021.[18] Having previously been assigned the number 30, Chilwell was given the squad number 3 for the2016–17 season.[19]
He made hisPremier League debut on 26 December in a 2–0 home defeat toEverton.[20] Five days later, he made his first home appearance in the Premier League, playing the full 90 minutes of a 1–0 win overWest Ham United.[21]
He made 19 appearances across the2016–17 season, including two in theUEFA Champions League, and scored his first career goal on 18 May 2017 in a 6–1 home loss to Tottenham Hotspur.[22]
During the2017–18 season, Chilwell became Leicester's first-choice left-back ahead ofChristian Fuchs.[23] Chilwell wassent off for the first time in his career on 13 January 2018 after receiving two yellow cards within five minutes of each other in a goalless draw away toChelsea.[24]
He signed a new six-year contract with Leicester on 20 October 2018[25] and, five days later, scored once and assisted two more goals in the team's record9–0 win away atSouthampton.[26]
On 9 November 2019, Chilwell made his 100th appearance for Leicester City in a 2–0 home win overArsenal in thePremier League.[27]
On 26 August 2020, Chilwell signed a five-year contract withChelsea, after Leicester City had accepted an offer for the player, reported byBBC Sport to be £45 million.[28] He made his debut on 23 September, providing the assist forOlivier Giroud's goal in a 6–0 home win againstBarnsley in the third round of theEFL Cup after he came off from the bench.[29] On his first league start for the club on 3 October, Chilwell scored the opening goal and assistedKurt Zouma for the second as Chelsea beatCrystal Palace 4–0 at home.[30]
On 2 October 2021, on his first Premier League start of the campaign, Chilwell scored his first goal of the season in a 3–1 home win overSouthampton.[34] Chilwell would go on to score in Chelsea's next two league games as well, 1–0 win againstBrentford and a 7–0 victory overNorwich City. Having scored in Chelsea's final match of the2020–21 Premier League season, Chilwell became the first English player to score in four consecutive Premier League games for Chelsea sinceFrank Lampard in February 2013.[35]
On 23 November 2021, Chilwell sustained a ruptured cruciate ligament injury in a 4–0 home win during Chelsea's2021–22 UEFA Champions League group stage match againstJuventus.[36] He was substituted in the second half after a coming together withAdrien Rabiot.[37] On 28 December 2021, it was revealed in a statement by Chelsea that Chilwell would have to receive a surgical repair, which ruled him out for the rest of the season.[38]
Chilwell signed a new contract with Chelsea on 11 April 2023, keeping him at the club until the summer of 2027.[39] In August, he was named as Chelsea's new vice-captain, acting as deputy toReece James.[40] On 25 February 2024, Chilwell captained Chelsea in the2024 EFL Cup final where they lost 1–0 toLiverpool.[41]
Chilwell's future with the club was cast into doubt in late August 2024 when new managerEnzo Maresca made clear the player was not in his plans, telling reporters "with (Chilwell), I said he is a lovely guy but with his position, he's going to struggle with us."[42] On 23 September, Maresca announced that Chilwell was back in the squad for theEFL Cup home tie againstBarrow the following day; he appeared as a 46th-minute substitute in a 5–0 win, which ended up being his only appearance for Chelsea of the season.[43]
On 3 February 2025, Chilwell joined Crystal Palace on loan for the remainder of the2024–25 season.[44] On 1 March, he was subjected to homophobic chants byMillwall supporters during thefifth round of the FA Cup, an incident which sparked an investigation bythe Football Association.[45] Crystal Palace defeated Millwall 3–1, and would eventually progress to thefinal; Chilwell was an unused substitute as the club went on to lift the FA Cup for the first time in its history following a 1–0 victory against Manchester City.[46] On 20 May, he scored his first goal for Palace in a 4–2 league win overWolverhampton Wanderers.[47]
Chilwell is the godfather to former Leicester City teammateJames Maddison's son.[60]
Chilwell was the victim of a campaign of harassment byTikToker Orla Melissa Sloan between 2021 and 2023. Sloan was convicted for harassment in June 2023, as well as of stalking Chilwell's former team-matesMason Mount andBilly Gilmour.[61]
^Sterling, Mark (11 August 2021)."Chelsea 1–1 Villarreal".BBC Sport.Archived from the original on 24 August 2021. Retrieved10 October 2021.
^"Chelsea 2–1 Palmeiras".BBC Sport. 12 February 2022. Retrieved1 April 2024. "Injured James & Chilwell get Club World Cup medals".Tribuna.com. 12 February 2022. Retrieved1 April 2024.Reece James and Ben Chilwell were unable to help their teammates in the Club World Cup due to injuries. But even without their first-choice wing-backs, Chelsea claimed the title and are now champions of the world. And both James and Chilwell received their Club World Cup medals!