There was a time when Chelsea’s lineup would have been reasonably easy to name, with players such as Petr Čech, John Terry and Frank Lampard being nailed-on starters for the Blues. Nowadays, however, things aren’t quite so simple. There have been numerous changes to the way that the club operates since Todd Boehly and Clearlake Capital bought the side from Roman Abramovich for around £2.5 billion in the summer of 2022. It means that working out the club’s longest-serving players isn’t an easy thing to do, given how much churn there seems to be in the playing squad.
Even so, here is a look at the players that have been playing for the Stamford Bridge side for the longest time come the start of the 2025-2026 season:
Reece James (2005-Present)
Reece Lewis James was born in Greater London on the eighth of December 1999. As a youngster, he played grassroots football for Kew Park Rangers and Epsom Eagles, but he was signed up to the Chelsea Academy when he was a six-year-old. Although he spent a year at Fulham’s Academy in 2007-2008, he returned to Cobham at the end of that and has remained on Chelsea’s books ever since. In his early years, he was a striker who idolised Didier Drogba, but was moved into midfield before later being turned into a right-back, in spite of initial struggles in the position.
In the March of 2017, James turned professional, soon being made the captain of the club’s Under-18s team that won the FA Youth Cup. After a year on loan at Wigan Athletic during the 2018-2019 season, he returned to Chelsea and has remained at the club since. His debut with the senior team came in the September of 2019, with injury plaguing his career from that point onwards. In spite of this, he was named the club captain thanks to being its longest-serving player in the wake of César Azpilicueta’s departure in 2023, lifting his first trophy in the role when Chelsea won the 2025 UEFA Conference League.
Trevoh Chalobah (2007-Present)
Born in Sierra Leone on the fifth of July 1999, Trevoh Tom Chalobah moved to England as a two-year-old. He joined the Chelsea Academy when he was eight, making his way through the ranks of the club and being part of the teams that won the UEFA Youth League and the FA Youth Cup in the 2015-2016 season, as well as the FA Youth Cup again and the Under-18 Premier League in the following campaign. When the Blues made it to the FA Cup final in 2018, he was named as a substitute for the game against Manchester United, but wasn’t called upon.
In the June of 2018, Chalobah signed a loan deal with Ipswich Town, heading to the Championship for the season. The following August, he signed a new contract at Stamford Bridge before heading to Huddersfield Town on another loan. A year later, another new contract was followed up by his third loan in as many years, this time to the French side Lorient. He was sent on loan to Crystal Palace in the August of 2024, but recalled by his parent club when a number of injuries were suffered to the defence. Although he’s a long-serving player, not much of that time has been spent actually playing for Chelsea.
Levi Colwill (2011-Present)
There were numerous different teams interested in signing Levi Lamar Samuels Colwill after he started to make a name for himself as a talented left-back. Born in Southampton on the 26th of February 2003, three of his uncles were footballers. He joined the Chelsea youth setup at the under-9 level, signing his first professional contract in the February of 2020. A little over a year later, Colwill was sent on loan to Huddersfield Town for the remainder of the season, scoring his first career goal for the Hatters against Sheffield United in a 2-1, only for his season to be interrupted by injuries.
Levi Colwill has signed a new six-year contract with Chelsea ✍️🔵 pic.twitter.com/2Ik1tNhtWG
— Sky Sports Premier League (@SkySportsPL) August 2, 2023
On the fifth of August 2022, he was sent out on loan to fellow Premier League side Brighton & Hove Albion, impressing the Seagulls enough to persuade them to bid £30 million for his services. Chelsea turned that down, giving him a new contract in 2023 that would keep him at Stamford Bridge until at least 2029. Although a centre-back by trade, he has played left-back for Chelsea numerous times, fitting in as needed. Sadly for the player, his career has been repeatedly blighted by injury, but he is young enough to mean that he can bounce back from such issues.
Raheem Sterling (2022-Present)
The fact that Raheem Sterling is one of Chelsea’s longest-serving players tells you quite a lot about the amount of turnover at Stamford Bridge. Born in Kingston, Jamaica on the eighth of December 1994, Sterling played for Alpha & Omega as a youngster before being signed up to the Academy of Queens Park Rangers in 2003. He remained there for seven years before joining the Liverpool Academy in 2010. It was in 2012 that he got his senior debut, aged 17 years and 107 days, going on to become an important part of Brendan Rodgers’ exciting attacking unit.
Having signed a contract extension in the December of 2012, he ended up leaving the Reds three years later to join Pep Guardiola at Manchester City. He became an important part of the dominant side, winning countless trophies before departing to join Chelsea in the summer of 2022.
The Blues paid just shy of £50 million for his signature, having been made the number one transfer priority of manager Thomas Tuchel, but within a couple of years the then-manager Enzo Maresca effectively said he didn’t want him. He went to Arsenal on loan for a season, but returned in the summer of 2025.