Charlton Athletic’s five most expensive sales include a Europa League champion and Intertoto Cup winner

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Charlton Athletic are preparing for their first season back in the Championship after six years away from the division, spending this time in League One.

They earned their place back in the Championship after beating Leyton Orient in the League One play-off final, helping increase the interest in their manager, Nathan Jones, who was then pursued by Cardiff City to become their next manager earlier this summer.

As the club prepares for life back in the second tier alongside fellow League One departees Birmingham City and Wrexham, making a significant impact will demand shrewd business in the transfer window.

Charlton do not have as big a transfer budget as the other two newly promoted League One clubs, and so they will need to make a number of sales to be able to bring in some fresh faces.

However, it is unlikely any of their departures this season will reach the similar fees to the five most expensive sales the club have made.

EFL Analysis brings you the five most expensive sales the club have ever made, according to Transfermarkt.

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5. Danny Mills – £5.2 million

Danny Mills joined Charlton in the summer of 1998 and spent only a season at the London club; however, he had a major impact that campaign.

The full back helped them win promotion that season, with Charlton beating Sunderland in the playoff final.

Mills would leave Charlton that summer to join Leeds United, who were splashing the cash at the time, with the full back being one that the Yorkshire club decided to bring in.

Following his departure from Charlton, Mills would go from strength to strength as he made 19 appearances for England after he made his debut in 2001.

4. Andy Reid – £5.2 million

The former Ireland international spent a season and a half at Charlton before leaving the club to join Sunderland for £5.2 million.

Andy Reid was part of the Charlton side that got relegated from the Premier League and spent half a season in the Championship before Roy Keane purchased him in January 2008.

He only featured in 40 matches during his time at Charlton, scoring nine goals, as he performed spectacularly throughout his time at the Valley, with Reid captaining the club in this period.

3. Ademola Lookman – £7.6 million

Everton spent heavily to bring Ademola Lookman to Merseyside from Charlton, when you take into account the London side were in League One at the time.

It would take Lookman two seasons to properly break into the Everton first team; however, in the third season, he played a key role for Everton.

Since leaving Everton, Lookman has gone on to become one of the most desirable wingers in the world following his performance in the 2024 Europa League final, as he scored a hat-trick for Atalanta against Bayer Leverkusen.

He has also become a Nigerian international since leaving Charlton in January 2017.

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2. Scott Parker – £12.6 million

Scott Parker came through the underage setup at Charlton and made his debut in August 1997 against Bury.

However, he would leave the club in January 2004 to join Chelsea, who had just been injected with investment from Roman Abramovich.

The West London club were happy to spend heavily to bring success, with Scott Parker being one of these investments.

An offer of £12.6 million was deemed acceptable by Charlton, after years of rumours linking Parker away from his boyhood club.

1. Darren Bent – £21.5 million

Darren Bent is the most expensive sale Charlton Athletic have ever made, when he departed the club for £21.5 million to join Tottenham Hotspur.

The striker spent two seasons at the club after joining from Ipswich Town in the summer of 2005 for £2.5 million.

Bent was Charlton’s top goal scorer for the two seasons he was at the club before joining Spurs in the summer of 2007.

His move was made easier by the fact that Charlton had been relegated from the Premier League the season prior to his move across London.