The 10 most expensive left-backs of all time

Daniel Edwards
Daniel Edwards
  • 13 Sep 2023 09:00 CDT
  • 3 min read
Marc Cucurella, Chelsea, 2023/24
© ProShots

Marc Cucurella became the most expensive player in his position after joining Chelsea in the summer of 2022, surpassing one of his team-mates and Man City's Benjamin Mendy.

Cucurella joined Chelsea in a move that will cost a total of £62 million, four times the £15.4m they paid to bring him to the Amex Stadium on deadline day less than 12 months earlier.

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The transfer entered the history books as the most expensive ever struck for a left-back, surpassing City's signing of Benjamin Mendy.

However, Cucurella has proved to be a flop at Chelsea and within a year was already surplus to requirements at Stamford Bridge.

Football's priciest left-backs

As for Mendy, he cost the Premier League side €57.5m in 2017 when he joined from Monaco, a move that in hindsight proved disastrous for the purchasers.

The player managed just 75 games for City in six seasons and was suspended for a chunk of that on rape allegations, which he was eventually cleared on. He left the club in 2023.

Chelsea currently occupy third place in the rankings for a player they signed in 2020.

Ben Chilwell in action for Chelsea in their Premier League win at Brentford
© ProShots

Ben Chilwell cost the Blues €50.2m when he arrived from Leicester City and was a fixture in the side that under Thomas Tuchel won the Champions League during his maiden season at the club.

In 2021-22, however, the full-back ruptured his cruciate ligament but he has since returned to form and fitness.

Real Madrid paid dearly for Ferland Mendy in 2019 as the anointed successor to club great Marcelo and the Frenchman has proved a smart acquisition as he has gradually made the starting role his own and won the Champions League in 2022.

Luke Shaw, Manchester United, 2021/22
© ProShots

Nuno Mendes arrived at Paris Saint-Germain in 2022 for €38.5m and has yet to push on at the club.

Meanwhile Luke Shaw, a previous holder of the title of most expensive left-back, is still at Manchester United nine years after the Reds paid Southampton €37.5m for his services.

You can find the full top 10 in the table below, but it is just as interesting to see who is missing: Marcelo and fellow Madrid idol Roberto Carlos, for example, do not even break the top 100, having cost the Merengue a grand total of €10m combined - truly two of the biggest bargains in football history!

The most expensive left-backs in football history

Marc CucurellaBrighton to Chelsea€73.5m2022-23
Benjamin MendyMonaco to Man City€57.5m2017-18
Ben ChillwellLeicester to Chelsea€50.2m2020-21
Ferland MendyLyon to Real Madrid€48m2019-20
Nuno MendesSporting to PSG€38m2022-23
Luke ShawSouthampton to Man Utd€37.5m2014-15
Oleksandr ZinchenkoMan City to Arsenal€35m2022-23
Lucas DigneEverton to Aston Villa€30m2021-22
Sergio ReguilonReal Madrid to Tottenham€30m2020-21
Fabio CoentraoBenfica to Real Madrid€30m2011-12

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