No matter what anyone tells you, always remember that transfers in football are a gamble. A team may very well carry out a due diligence to the best of their ability when scouting a player, only for the ensuing move to not work out for a variety of reasons.

In this article, we present to you our top 5 picks for the worst signings Tottenham have made in the Premier League era.

Tanguy Ndombélé

Let’s get this one out of the way first. In an age where three-figure sums are a dime a dozen in football, Spurs’ most expensive player holds a price tag of £65 million. Before Dominic Solanke moved to Spurs this summer, however, the Lilywhites’ most expensive acquisition was at €62 million.

Given Daniel Levy’s infamous frugality, eyebrows were naturally raised when Spurs went above and beyond to get Ndombélé, but the move ultimately blew up in their collective face. Apart from fleeting moments of brilliance, he never quite found his feet in the PL, having been deemed not good enough consistently by every manager at Spurs. Ndombélé spent the last years of his Spurs contract on loan at Lyon (2022), Napoli (2022/23), and Galatasaray (2023/24) before joining Nice this summer as a free agent.

Roberto Soldado

There were a fair few players Spurs spent the Gareth Bale money on, most of whom did not work out. One of them was Roberto Soldado, who arrived at White Hart Lane with quite the pedigree, having been one of LaLiga’s best forwards and a leader at Valencia at the time.

Sadly, none of it followed him on his journey to England. Soldado made 76 appearances for Spurs in the two seasons he represented them, in which he delivered just 16 goals and 11 assists. Having spent €30 million on him, Spurs promptly sent him back to Spain two years later as Villarreal snapped him up for €16 million.

Ryan Sessegnon

This is a harsh and yet unavoidable call. Ryan Sessegnon had the world at his feet after the end of the 2017/18 season, in which he spearheaded Fulham’s promotion charge from left-wingback as a teenager, delivering 16 goals and 8 assists in 52 appearances across all competitions. His performances duly earned him the EFL’s Young Player of the Year and Championship Player of the Year awards for the season, and it was considered quite the coup by Spurs when they picked him up that summer for €27 million.

Alas, it wasn’t to work out. Apart from a brief period under Antonio Conte, Sessegnon never really got going at Spurs. Apart from spending a season out on loan at German side Hoffenheim, Sessegnon represented Spurs just 57 times. He returned to Fulham earlier this summer as a free agent.

Vincent Janssen

This one is quite the stinger. One can be forgiven for not remembering that Janssen was the best player in the Netherlands when Spurs poached him from AZ Alkmaar for €22 million, having registered a modest 32 goals and seven assists in 49 appearances during the solitary season he spent at AFAS Stadion.

There was nothing wrong with this move on paper, but it still simply did not work out. Harry Kane had already established himself as the indisputable first-choice striker at the club, and whatever chances Janssen received, he failed to impress in them. He was loaned out Fenerbahçe for the 2017/18 season and ultimately sold to Mexican side Monterrey in 2019.

During his time in North London, Janssen made 42 appearances across all competitions, scoring six goals and assisting four times.

Kevin-Prince Boateng

Having hung up his boots last year, it is safe to say the former Ghana international has had a much-travelled, fairly successful career. The same cannot be said about his time at Tottenham, however. Arriving from Hertha Berlin in 2007 for €7.9 million, he thoroughly failed to impress in the 24 appearances he made during his time at North London, registering just one assist.

Boateng remained on Tottenham’s books for two years, spending the last half-year on loan at Dortmund. He was promptly shipped off to Portsmouth in 2009 for €4.5 million.

What do you make of this list? Do you think some other Spurs signing deserves a shout? Tell us in the comments.