#3 Pop Robson (36 years, 11 months and 16 days)
Bryan "Pop" Robson was a successful English striker of the 20th century. He featured for Newcastle United, West Ham United, Sunderland and Carlisle before joining Chelsea in July 1982 aged 36.
Robson was in the twilight of his career when he signed for Chelsea and he only managed 17 appearances for the club, scoring five goals. The striker scored his last goal for the club on his last appearance, a 5-2 defeat at the hands of Charlton Athletic on March 5, 1983.
Robson moved back to Carlisle United on loan, after which he joined Sunderland and Gateshead before his retirement in 1986. He turned to coaching at the end of his professional playing career.
#2 Didier Drogba (37 years, 1 month and 18 days)
Regarded as the King of Stamford Bridge, Didier Drogba is one of the best late bloomers the world has ever seen in football. The Ivorian striker joined Chelsea from Olympique Marseille in 2004 before earning legendary status in the Premier League.
Drogba had two spells as a Chelsea player. In his first spell, he scored the winning penalty on his last appearance for the club to win them the 2012 UEFA Champions League. He returned in the 2014-15 season and helped the side win the Premier League that season. His last goal for the club came in a 3-1 win over Leicester City on April 29, 2015.
Drogba played for Montreal Impact and Arizona United in North America before finally retiring in 2018. The striker is one of the most prolific in the club's history.
#1 Thiago Silva (37 years, 4 months and 1 day)
When Frank Lampard sanctioned a move for Thiago Silva in 2020, eyebrows were raised over his age. The Brazilian has done exceptionally well to shoot down any such worries as a Chelsea player.
Silva scored his most recent Chelsea goal in their 2-0 win over Tottenham Hotspur on January 23, 2022 in the Premier League. The 37-year-old defender only recently extended his contract at the club by one more year and will play till he's 38 years old.
Silva has made 65 appearances for Chelsea since joining the club. He has also found the back of the net five times in this period.