Spurs have made headlines in recent years for its series of positive and negative transfer signings. Everyone knows that Tottenham is not afraid to make big investments to acquire suitable talent for its football club. While some of those investments have paid off well for the club, others have been disastrous.
Here are some notable Tottenham Spurs transfer updates that have resulted in major triumphs and regrets for the famous football club.
The £40 Million Deal for James Maddison
In June 2023, Tottenham signed a transfer contract and paid £40 million to acquire James Maddison from Leicester City. The famous attacking midfielder has been playing professional football since 2016, playing with Norwich City for two years before transferring to Leicester City in 2018. Three years later, he won the FA Community Shield and FA Cup.
Maddison agreed to sign for Tottenham in 2023. For the most part, the transfer turned out to be a success for Tottenham. At a time when Tottenham’s midfield game needed improvement, Maddison leveraged his skill and leadership as a midfielder to win his first game with Tottenham. Unfortunately, Maddison suffered an ankle injury on November 6th, 2023, only three months after starting his first game with Tottenham. The injury forced him onto the sidelines for the rest of the year. He returned to play in 2024.
The £42 Million Deal for Cristian Romero
In August 2022, Argentine professional footballer Cristian Romero transferred from Atalanta BC to Tottenham Hotspur after signing a five-year contract worth £42 million. Romero is best known as an aggressive defensive centre-back with incredible ball-playing ability, tackling skills, and aerial dominance on the field.
Tottenham originally acquired Romero on loan from Atalanta in 2021. However, after Romero made significant improvements to Tottenham’s backline defence, the club decided to sign a deal to make him a permanent team member.
This has proven to be a very successful decision because Romero has become one of Tottenham’s best defenders.
The £30 Million Deal for Yves Bissouma
In June 2022, Malian professional footballer and defensive midfielder Yves Bissouma signed a £30 million, four-year contract deal to play for Tottenham. Unfortunately, Bissouma suffered multiple injuries during his first few months with the club. The good news is that he was able to make a quick recovery after each injury.
Throughout the 2023/2024 season, Bissouma excelled as a midfielder under the intense management of Ange Postecoglou. His impressive ball-winning abilities have made him an asset for Tottenham. He won two consecutive Man of the Match performance awards after playing against Brentford and Manchester United in his first two matches.
The £54 Million Deal for Tanguy Ndombele
In July 2019, Tottenham signed a record-breaking deal worth £54 million to acquire French professional football midfielder Tanguy Ndombele from Lyon. It was a six-year contract that Tottenham likely ended up regretting since they mutually agreed to terminate his contract in 2024 before it expired.
Ndombele had some notable moments on the field during his five years with Tottenham. The problem was that his performances were inconsistent due to his apparent struggles to maintain proper fitness and form. At first, Tottenham loaned Ndombele back to Lyon in 2022 because he wasn’t living up to their expectations. Then, they loaned him to Napoli and then Galatasaray.
In 2024, the French football club OGC Nice purchased Ndombele through a two-year contract. He ended up becoming one of Tottenham’s biggest transfer investment failures in modern history.
