June 19, 2025

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Now worth £21m less: Spurs must regret making "ridiculous" 2020 signing

Now worth £21m less: Spurs must regret making “ridiculous” 2020 signing

Like all clubs, Tottenham Hotspur have made their share of costly and poorly considered signings over the years.

Players such as Richarlison, Tanguy Ndombele, and Giovani Lo Celso are not necessarily bad players, but their transfers turned out to be expensive mistakes, with little return on investment.

However, aside from Richarlison, the club has managed to offload most of these unsuccessful acquisitions in recent seasons.



That said, there is one player who joined in 2020 for a significant fee but has since seen his value plummet. When he eventually leaves, Tottenham will likely incur a substantial financial loss.

Tottenham’s 2020 Signings

It’s fair to say Tottenham’s 2020 signings were a mixed bag, though describing them as such might suggest a few successes, which weren’t really the case—apart from the return of Gareth Bale on loan.


The Welsh legend returned to North London for the 2020/21 season. While he wasn’t the same player who left, he still contributed well to the squad.

Over 34 appearances and 1680 minutes, Bale scored 16 goals and provided three assists, averaging a goal involvement every 1.78 games or roughly every 88 minutes.

On the other hand, one of the summer’s less successful signings was Matt Doherty, who arrived from Wolverhampton Wanderers for £14.7m.

Unfortunately, Doherty struggled to make an impact, featuring in just 71 matches over two and a half seasons before having his contract mutually terminated in January 2023. He later joined Atlético Madrid, but his time there was also unsuccessful.

Despite Doherty’s failure at Spurs, the club was able to part ways with him early and minimize their losses. The same can’t be said for another signing from that summer.

The Signing Worth Much Less Today

Other signings from the summer of 2020, such as Carlos Vinicius and Joe Rodon, didn’t quite work out, but they didn’t cost Spurs too much in the long run. Sergio Reguilón, however, is a different story.



Reguilón was signed in September 2020 for around £28m. Initially, he made a positive impression, featuring 36 times in his first season, providing five assists.

He then retained his place as the first-choice left-back for most of the following campaign, making 31 appearances, scoring two goals, and adding three assists.

However, Reguilón’s fortunes took a downturn after suffering a groin injury, and at the start of the next season, he was loaned out to Atlético Madrid.

His time in Spain was marked by injuries and subpar performances, as he only made 12 appearances across all competitions.

In the following year, Reguilón had loan spells with Manchester United and Brentford, featuring in just 12 and 16 games, respectively.

His time at Brentford was particularly forgettable, highlighted by a poor challenge in a match against West Ham United that led Gary Neville to label him as “absolutely ridiculous.”

This season, Reguilón has remained in North London, but it’s clear that manager Ange Postecoglou has little faith in him.

Despite being fit, Reguilón has only played 242 minutes across five appearances, with most of that likely due to a defensive injury crisis at the club.



As a result, Reguilón’s value has plummeted. Football Transfers now estimates his worth at just €8.5m (around £7m), a staggering £21m loss from the £28m Tottenham paid for him in 2020.

While signings can fail, it’s hard not to imagine that Tottenham would have been better off selling Reguilón at a loss a couple of years ago.

With his £53,000-a-week contract set to expire in the summer, it seems likely that he will leave for nothing, further compounding the financial blow.

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