Ranking Tottenham’s Biggest Transfer Deals Since 2018
Tottenham have been one of the Premier League’s most unpredictable clubs in recent years, often mixing moments of brilliance with stretches of underachievement. Since 2018, the club has spent heavily in the transfer market in an effort to build a squad capable of challenging for trophies.
With such significant investment, expectations have been high—but the results have been mixed. Some signings have proven to be game-changers, while others have failed to make an impact.
We’ve taken a closer look at Spurs’ biggest transfers since 2018, ranked them by transfer fee, and judged whether each deal was ultimately a hit or a miss.
22. Matt Doherty – £15M – MISS
Signed from Wolves to bring attacking depth at right-back, Doherty never truly fit into Spurs’ system. Inconsistent form and limited impact saw his contract terminated early.
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21. Emerson Royal – £21M – MISS
Despite ample game time since arriving from Barcelona, Emerson has struggled to convince defensively and offensively. Fans and pundits alike remain divided over his performances.
20. Bryan Gil – £21M – MISS
A highly-rated talent from Sevilla, Gil failed to adapt to the Premier League’s physicality and was loaned out multiple times without making a serious mark in North London.
19. Rodrigo Bentancur – £22M – HIT
A shrewd signing from Juventus, Bentancur brought much-needed composure and balance to midfield. Injuries aside, he’s proven to be a reliable and intelligent presence.
18. Wilson Odobert – £25M – MISS
A surprising signing from Burnley in 2024, Odobert hasn’t shown enough to justify his fee. Still raw, he’s yet to deliver meaningful contributions at the top level.
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17. Ryan Sessegnon – £25M – MISS
Tipped for stardom after joining from Fulham, Sessegnon has been plagued by injuries and inconsistency. He’s yet to cement a regular place or fulfill his early potential.
16. Lucas Moura – £25M – HIT
The hero of the 2019 Champions League semifinal against Ajax, Lucas had flashes of brilliance throughout his time at Spurs. His legacy is defined by clutch moments.
15. Radu Dragusin – £25M – MISS
Signed from Genoa in 2024, Dragusin was brought in to bolster the defense but has yet to earn regular starts or establish himself as a Premier League-caliber center-back.
14. Giovani Lo Celso – £27M – MISS
A creative midfielder from Real Betis, Lo Celso showed promise but lacked consistency. Injuries and tactical mismatches limited his influence at the club.
13. Sergio Reguilon – £27M – MISS
Coming from Real Madrid with high hopes, Reguilon started brightly but quickly faded. Defensive lapses and competition for his position pushed him out of favor.
12. Steven Bergwijn – £27M – MISS
The Dutch winger had some memorable goals but never found consistency. Often a bench option, he eventually left without fulfilling the expectations of his fee.
11. Dejan Kulusevski – £29.2M – HIT
A dynamic attacker from Juventus, Kulusevski brought energy and creativity. His strong link-up play and versatility have made him a key figure in Spurs’ frontline.
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10. Archie Gray – £30M – HIT
One of England’s brightest young talents, Gray impressed immediately after joining from Leeds. His maturity and technical quality suggest a big future ahead.
9. Yves Bissouma – £30M – MISS
Dominant at Brighton, Bissouma has failed to replicate that form at Spurs. Erratic displays and limited impact have made his time underwhelming so far.
8. Pedro Porro – £37.5M – HIT
An attacking right-back from Sporting, Porro has added width, pace, and quality in the final third. He’s quickly become a fan favorite with consistent performances.
7. James Maddison – £40M – HIT
Signed from Leicester, Maddison instantly improved Spurs’ creativity and tempo. His vision, set-pieces, and leadership have been instrumental when fit.
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6. Micky van de Ven – £43M – HIT
A commanding and fast center-back, van de Ven has transformed the backline. His composure and recovery pace make him one of the most reliable defenders in the squad.
5. Cristian Romero – £47M – HIT
Aggressive and uncompromising, Romero was a vital addition from Atalanta. He’s brought bite and leadership to Spurs’ defense, becoming a regular starter.
4. Brennan Johnson – £47.5M – HIT
Pacey and direct, Johnson joined from Nottingham Forest and quickly settled in. His ability to stretch defenses and contribute in big games makes him a valuable asset.
3. Tanguy Ndombele – £55M – MISS
Spurs’ record signing for years, Ndombele dazzled in flashes but lacked discipline, fitness, and consistency. He’s been loaned out repeatedly and remains a huge disappointment.
2. Dominic Solanke – £55M – HIT
Brought in from Bournemouth in 2024, Solanke has delivered with goals and physical presence up front. He’s offered something different and filled a major need in attack.
1. Richarlison – £60M – MISS
The most expensive signing in club history, Richarlison has failed to live up to expectations. Despite opportunities, his goal return and influence have been far below what was hoped for.
