Chelsea's oldest signings ever: Where Henderson and Welbeck rank after Stamford Bridge moves

For a club that spent much of the past decade assembling one of the youngest squads in Premier League history, Chelsea's transfer business under Xabi Alonso marks a notable change in direction.

The imminent arrivals of Jordan Henderson, 36, and Danny Welbeck, 35, represent a clear shift towards experience and would see both players rank among the oldest footballers ever to sign for the Blues.

With reports that both deals are in their final stages, Sports Mole takes a look at where Henderson and Welbeck would sit among Chelsea's oldest signings.

Mark Schwarzer – 40 years old

The oldest player Chelsea have signed in the Premier League era, Mark Schwarzer arrived on a free transfer from Fulham in the summer of 2013 at the age of 40.

Although Petr Cech remained first choice and Thibaut Courtois returned from his loan spell a year later, the Australian proved to be an invaluable presence around the squad.

Schwarzer made 12 appearances across two seasons, including four in the Premier League, while his professionalism and experience earned widespread praise from Jose Mourinho.

He also became the oldest player to represent Chelsea in the Champions League when he featured against Atletico Madrid in the 2013-14 semi-finals.

Robert Green – 38 years old

Five years after Schwarzer's arrival, Chelsea again turned to experience between the posts by signing Rob Green on a free transfer from Huddersfield Town.

Green never made a competitive appearance during his sole season at Stamford Bridge, serving as third-choice goalkeeper behind Kepa Arrizabalaga and Willy Caballero under Maurizio Sarri.

His contribution came almost entirely behind the scenes, as he remained an experienced figure in the dressing room.

Didier Drogba (second spell) – 36 years old

Didier Drogba's return to Stamford Bridge in 2014 was driven as much by leadership as sentiment, with Mourinho bringing one of Chelsea's greatest-ever players back to west London after his spell at Galatasaray.

Although he was no longer the talismanic striker who had inspired Chelsea to Champions League glory in 2012, Drogba still played an important role during the 2014-15 campaign, scoring seven goals in 40 appearances as the Blues won the Premier League and League Cup.

His influence extended well beyond his performances on the pitch, providing invaluable experience in a title-winning dressing room.

Jordan Henderson – 36 years old (incoming)

Should his move from Brentford be completed as expected, Henderson will become one of the oldest outfield players Chelsea have signed in the modern era.

The former Liverpool captain arrives after rebuilding his reputation following difficult spells at Al-Ettifaq and Ajax, bringing leadership, tactical intelligence and close to 800 senior appearances at club and international level.

While his legs may not cover quite as much ground as they once did, Chelsea will hope his experience can help guide one of the Premier League's youngest squads through another demanding campaign.

Willy Caballero – 35 years old

Signed from Manchester City in 2017, Willy Caballero proved to be a dependable deputy across four seasons in west London.

The Argentine goalkeeper made 38 appearances and kept 14 clean sheets, providing reliable cover whenever called upon.

He was denied an appearance in the 2019 EFL Cup final after Kepa Arrizabalaga refused to leave the pitch despite Maurizio Sarri attempting to substitute him, but Caballero remained an important member of Chelsea's goalkeeping group throughout his stay.

Danny Welbeck – 35 years old (incoming)

Welbeck's expected arrival follows arguably the finest goalscoring season of his career, having enjoyed an outstanding campaign with Brighton & Hove Albion before agreeing to join Chelsea.

Never a striker judged solely on goals, Welbeck has built his career on intelligent movement, tireless pressing and excellent link-up play.

Across six seasons with Brighton, he developed into one of the Premier League's most reliable all-round forwards, and Chelsea will hope his recent form and wealth of experience can provide another valuable option in attack.

Thiago Silva – 35 years old

Few Chelsea signings have exceeded expectations quite like Thiago Silva.

When the Brazilian arrived on a free transfer from Paris Saint-Germain in 2020 at the age of 35, there were understandable questions over whether he could still cope with the pace and intensity of English football.

Instead, Silva became one of the club's most successful late-career signings, helping Chelsea win the Champions League in his first season before making more than 150 appearances across four years.

Named Chelsea's Player of the Season for 2022-23, Silva set the benchmark for experienced signings at Stamford Bridge, combining leadership and world-class quality throughout his time at the club.

Olivier Giroud – 31 years old

Olivier Giroud's January 2018 move from Arsenal initially divided opinion, but the Frenchman quickly established himself as one of Chelsea's most effective forwards.

He scored 39 goals in 119 appearances and helped the Blues win both the Europa League and Champions League.

Giroud also finished as Chelsea's leading scorer in their triumphant 2020-21 Champions League campaign with six goals, including four in a memorable group-stage victory over Sevilla.

His ability to deliver in the biggest moments ensured he left Stamford Bridge as one of the club's most respected modern signings, proving that experience can be just as valuable as youth when surrounded by the right squad.