Five Unforgettable Cup Matches Between Arsenal and Chelsea

Chelsea and Arsenal will face off tonight in the Carabao Cup semi-finals at Stamford Bridge, looking to gain an advantage in this first leg.

As the teams prepare, we’ve highlighted five notable cup matches between them.

Chelsea 0-2 Arsenal, FA Cup final (May 4, 2002)

In 2002, Arsenal defeated Chelsea in the FA Cup final at Cardiff, marking their journey toward a domestic double.

The match sparked to life when Ray Parlour scored in the 69th minute with a stunning shot into the top corner. Ten minutes later, Freddie Ljungberg secured the win with another impressive goal, finishing past Carlo Cudicini. Ljungberg became the first player in four decades to score in consecutive finals after netting in the previous year’s match against Liverpool.

Arsenal soon completed their domestic double a few days later when Sylvain Wiltord scored the decisive goal to win the Premier League against Manchester United.

Arsenal 1-2 Chelsea, Champions League quarterfinal second leg (April 6, 2004)

In their Champions League meeting during the 2003/04 season, Arsenal were on track to finish the Premier League unbeaten, but faced a tough European exit.

Despite having not beaten Arsenal in 17 matches, Chelsea equalized after going down to an early goal by Jose Antonio Reyes. Frank Lampard leveled the score, but Wayne Bridge scored a late winner, sending Chelsea through.

Wayne Bridge. Highbury. 6 April 2004. 🤩#onthisday pic.twitter.com/c9ET18U38G

— Chelsea FC (@ChelseaFC) April 6, 2020

The takeover of Chelsea by a billionaire the previous summer began to shift the dynamics of London football.

Chelsea 2-1 Arsenal, League Cup final (February 24, 2007)

This final was intense, with three players — John Obi Mikel, Emmanuel Adebayor, and Kolo Toure — receiving red cards after a brawl.

The match saw an under-manned Arsenal take the lead through Theo Walcott, but Chelsea equalized with a goal from Didier Drogba. In the end, Drogba’s late header off an Arjen Robben cross secured the victory for Chelsea.

#OTD in 2007, Drogba scored a delightful double against Arsenal to secure us a fourth League Cup! 🫡#CFC | #CarabaoCupFinal pic.twitter.com/OWoWx8gIlL

— Chelsea FC (@ChelseaFC) February 25, 2024

Arsenal 2-1 Chelsea, FA Cup final (May 27, 2017)

Arsene Wenger made history by winning the FA Cup for a record seventh time in 2017.

Arsenal took the lead with a controversial goal from Alexis Sanchez, which the referee allowed despite an offside call. Chelsea faced additional challenges when Victor Moses was sent off for diving. Diego Costa equalized, but Aaron Ramsey scored the winning goal for Arsenal shortly after.

Chelsea 4-1 Arsenal, Europa League final (May 29, 2019)

Eden Hazard had a standout match in his final appearance for Chelsea, scoring two goals against Arsenal in the Europa League final held in Baku.

This was the first time the two teams met in a European final, and Chelsea dominated the match. After a scoreless first half, Olivier Giroud opened the scoring, followed by a goal from Pedro. Hazard then netted a penalty and added another goal to secure a commanding win for Chelsea.