Chelsea's top 10 most expensive transfer sales – ranked

Chelsea have long been kings of the transfer market, whether it be by splashing the cash or by receiving impressive fees for not-so-impressive players.

For a club whose history of collecting plenty of value for players is quite extensive, the bar is relatively high for those aiming to reach the top 10.

Here, we’ve put together that very list, with Chelsea’s biggest departures ranging from star players to transfer flops.

All information is correct as of 17th October 2025. Transfer fees have been obtained from news reports, with add-ons included where applicable.

Nemanja Matic’s departure was a slightly peculiar one off the back of their successful 2016/17 Premier League campaign.

The Serbian midfielder missed just three games as Chelsea romped to the title under Antonio Conte, but he was soon off to rivals Manchester United to link up with former Blues boss Jose Mourinho.

Chelsea did at least gain £40m from the deal, though they haven’t hit the same heights since his Stamford Bridge exit.

It could be argued that both of Joao Felix’s stints at Chelsea were a disaster. His first was marred by an embarrassing debut, where he was sent off, and amid a raft of changes following the change in ownership, Joao Felix was just a small part of the chaos that had engulfed the west Londoners.

His permanent (albeit short-lived) return also came about in strange circumstances, with Chelsea effectively opting to buy him from Atletico Madrid after selling Conor Gallagher to the Spaniards, largely to help comply with the Premier League’s PSR rules.

And despite only being handed a handful of starts by Enzo Maresca, Chelsea were still able to cash in when, after a loan move to Milan, the opportunity for the Portuguese playmaker to link up with Cristiano Ronaldo arose.

David Luiz became the world’s most expensive defender at the time of his 2014 exit from Chelsea, with PSG breaking their own record to seal a £50m deal (although some sources state the eventual figure was closer to £40m).

Chelsea were able to reinvest wisely that summer, and secured another league title under Mourinho despite letting the Brazilian go.

The Blues were even able to secure his return a few years later, joining for £34m in the summer of 2016.

Following in the footsteps of Jorginho and Kai Havertz, Madueke joined the Gunners for a substantial fee, presumably with his first-team prospects at Chelsea dwindling ahead of the World Cup.

Madueke only spent two and a half seasons at Chelsea – not even halfway into his seven-year deal.

After falling out with Antonio Conte, Diego Costa was sent packing by the then-champions despite helping the Blues to a second league title in three years.

And it was former club Atletico Madrid who came calling for the Spain international, with Diego Simeone’s side even happy to pay more than Chelsea did two and a half years prior to land the west Londoners a healthy profit.

It was yet another example of Chelsea getting more than they ought to in the transfer market – Costa went on to score just seven times after waiting three months to get his move back to Atletico.

Another player arguably overpaid for by Atletico Madrid was Alvaro Morata, who saw a disappointing spell at Stamford Bridge come to an end just 18 months after signing for a record fee.

Somehow, Chelsea still managed to recoup the best part of their £60m outlay, with Atletico Madrid bringing in the Spaniard on loan before his move was made permanent ahead of the 2020/21 season.

From there, most of Morata’s successes were for Spain rather than at club level, vindicating Chelsea’s choice to sell up so soon.

Oscar was one of the few players to arguably make a success of his move to the Chinese Super League, which attempted to pick off unwanted European-based talents in a similar vein to the Saudi Pro League when its financial might emerged some years later.

The Brazilian was well-liked in west London, but opted to follow the money the CSL could offer him. He eventually left with a reported £175m in the bank, meaning he could pay his handsome transfer fee from Chelsea nearly three times over.

Part of the fallout of Chelsea’s disastrous 2022/23 campaign saw one of their academy stars leave for big money.

Mason Mount left for Manchester United for an initial £55m, with £5m in add-ons. Mount had made his name at the club following a loan spell at Derby County, but saw his Stamford Bridge career end in April 2023, suffering a season-ending injury with the Blues stuck in mid-table.

Mount’s fitness issues continued following his move, making Chelsea’s deal rather pleasing from a financial perspective.

Amid the hordes of players arriving at Stamford Bridge, it was only natural that players would leave in order to balance the Blues’ books a little.

However, Kai Havertz – a Champions League winner and a heavy investment back in 2020 – may not have been top of the list of expected outgoings at Chelsea.

To add insult to injury, it was London rivals Arsenal who offered to take the German off their hands and went on to spearhead the Gunners’ title charge in 2023/24 – arguably leaving both sides happy with the heavy fee going Chelsea’s way.

The deal to sell Eden Hazard to Real Madrid could have gone better for Chelsea. Leaving with their blessing after steering the club to Europa League glory in 2018/19, the Belgian was a big target for Real Madrid, who were happy to part with €100m (£89m) upfront.