Chelsea vs. Ajax: Head-to-head record and past meetings

Chelsea secured a fourth straight win when they welcomed Ajax to Stamford Bridge in a matchday three clash in the Champions League league phase on Wednesday night.

An action-packed first half saw Chelsea enter the break leading by four goals to one, with Tyrique George quickly adding a fifth just after the second half restart to seal a comprehensive 5-1 victory.

Here, Sports Mole takes an in-depth look at the head-to-head record and previous meetings between the two sides.

Head-to-head record

Previous meetings: 3

Chelsea wins:2

Draws: 1

Ajax wins: 0

The 2025-26 Champions League league-phase clash between Chelsea and Ajax marked just the third competitive showdown between the English and Dutch powerhouses, who first collided in the group stage of the 2019-20 edition.

The Blues navigated both of those battles unbeaten, firstly conquering Erik ten Hag's men 1-0 in Amsterdam before an extraordinary eight-goal thriller at Stamford Bridge just a couple of weeks later.

Frank Lampard's Chelsea travelled to the Johan Cruijff ArenA in October 2019 for their inaugural competitive meeting with Ajax, who still boasted the likes of Lisandro Martinez, Donny van de Beek, Andre Onana and Hakim Ziyech in their side at the time.

A goalless draw was on the cards with five minutes of normal time remaining, but in the dying embers of the match, Chelsea substitute Michy Batshuayi received Christian Pulisic's pass and fired home the only goal of the game.

Fans might have been forgiven for expecting a similarly low-scoring scrap at Stamford Bridge two weeks later; the West London reunion was anything but, however, as Lampard and Ten Hag oversaw an engrossing 4-4 stalemate.

A Tammy Abraham own goal inside the second minute was a sign of things to come in the English capital, where the striker was bailed out just three moments later by a Jorginho penalty kick.

Everything that could go wrong for Chelsea did go wrong for Chelsea in the next hour or so, though, as Kepa Arrizabalaga also turned the ball into his own net either side of strikes from Quincy Promes and Van de Beek, propelling Ajax into a scarcely believable 4-1 lead.

However, Cesar Azpilicueta's response and Joel Veltman's red card sparked a colossal Chelsea comeback, in which Jorginho's second penalty of the game and an equaliser from Reece James drew the curtain on a chaotic contest.

A similar action-packed encounter unfolded in their third meeting in 2025-26, with the Blues running out 5-1 winners over Ajax in an affair that saw Kenneth Taylor sent off and goals from Marc Guiu, Moises Caicedo, Wout Weghorst, Enzo Fernandez, Estevao and George.