Special Relationship: The Players Who Have Moved Between Chelsea And Arsenal

For two rivals, Arsenal and Chelsea sure do a lot of business
13:00, 21 Oct 2023

Everyone in football knows that you shouldn’t strengthen your rivals. Whether it be localised ill-feeling or a battle for league places, it is accepted wisdom that you don’t sell players to your closest competitors. Yet it happens more than you’d think. There are two clubs in particular who are no strangers to sharing a negotiating table. Two clubs who meet in the Premier League this weekend: Arsenal and Chelsea.

The clubs are both London-based, which invites a certain amount of local rivalry even if they aren’t each other’s biggest rivals in the capital. They have also spent much of the last couple of decades duking it out for the same prizes, whether that be league titles, domestic and continental silverware or European places. If there were ever two teams that shouldn’t sell to each other, it’s Chelsea and the Gunners.


However, they frequently collaborate on deals. On deadline day tlast January, Jorginho left Stamford Bridge for the Emirates in a package that could rise to £12 million. The midfielder’s cross-city move was far from the first such interaction between the two clubs. Here’s five other deals between Arsenal and Chelsea in recent years. It should be noted, Willian’s move to the Gunners in 2020 was not included as it was a free transfer following the expiry of the Brazilian’s contract. The transfers covered here were all the result of direct dealings between Arsenal and Chelsea.

Ashley Cole to Chelsea and William Gallas to Arsenal

The first transfer you think of when recalling transfers involving these two clubs. The “Cashley Cole” saga saw the phrase “tapping-up” enter the footballing lexicon, used to describe a meeting between Cole and his representatives and the Chelsea hierarchy.

The bitter negotiations dragged on throughout the 2006-07 summer window, eventually culminating with Cole moving to Stamford Bridge and William Gallas going the other way. In another wrinkle to this sensational story, Chelsea released a statement claiming Gallas had threatened to score own goals against the club if he wasn’t allowed to move to Arsenal.

David Luiz

One of modern football’s greatest enigmas. Is it possible to be a great footballer but a terrible defender? Was he the genius who scooped trophies at five different clubs or the muppet responsible for Brazil getting annihilated 7-1 by Germany? And why was he so intent on killing Bart Simpson?

Whatever you think of the mercurial Brazilian, it still felt odd when Chelsea sold their Champions League winning centre back to the Gunners in 2019. Uncharacteristically for Luiz, his tenure wasn’t massively eventful. An FA Cup win and 73 appearances across two seasons made him a solid investment, even if Arsenal fans weren’t sad to see the back of him when he went to Flamengo in 2021.

Olivier Giroud

The World Cup winning forward enjoyed a decorated and prolific spell in North London. 105 goals across 250 games was a superb return even if Gunners fans seemed to only truly appreciate his skills when he had gone. 

Stamford Bridge was the next stop for Giroud, where he enjoyed a more mixed time of things. While his best seasonal goal return in the Premier League was eight, he did score some vital goals. His opener in the 2019 Europa League final helped his side to a 4-1 win over former club Arsenal, while he also lifted the FA Cup and Champions League in west London.


Petr Cech

A legendary figure at Stamford Bridge, Cech was a central part of Chelsea’s transition from cup team to Premier League title winners. Apart from the Club World Cup, Cech won every piece of silverware available to him at Stamford Bridge over the course of 494 appearances.

Cech kept his reputation as one of the world’s finest goalkeepers intact while at Arsenal, picking up the FA Cup while at the Emirates. In a cruel irony, his final club game was the 4-1 Europa League loss to Chelsea. Despite the heavy defeat, many advocated for Cech as Arsenal’s Man of the Match on the night.

Yossi Benayoun

Proof of just how closely these two sides have worked together, they managed to hash out a loan deal for Yossi Benayoun in 2011. The Israel international had joined Chelsea from Liverpool the year before, but failed to make an impact in west London.

Arsenal brought the midfielder in on a season long loan which ended in some success. Benayoun made 19 league appearances, netting four goals. His strike on the final day of the season helped the Gunners to a 3-2 win over West Bromwich Albion that saw them pip north London rivals Tottenham Hotspur to third place.

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