Tottenham Hotspur have made some fantastic signings throughout their history, from Danny Blanchflower and Jimmy Greaves to Gareth Bale and Son Heung-min.
But not every Spurs signing goes to plan, as the following flops demonstrate...
32. Jason Dozzell
A stalwart for Ipswich during a 10-year spell in the first team at Portman Road, Dozzell jumped ship to Spurs in a deal worth £1.9m in 1993.
The midfielder struggled to make the step up, though, and while he racked up more than 100 appearances in all competitions over the next four years, Dozzell rarely convinced. Spurs supporters would argue he found his level when he joined Northampton in 1997.
31. Kazuyuki Toda
Toda started all four of Japan’s games at the 2002 World Cup as the co-hosts reached the round of 16. He was on the move to Europe a year later when Tottenham agreed a deal to sign the midfielder on an initial loan from Shimizu S-Pulse.
It soon became clear Toda was out of his depth. He played only four times in the Premier League before Spurs shipped him back to Japan.
30. John Scales
Gerry Francis pushed for the acquisition of Scales, a player he had worked with at Bristol Rovers. The defender arrived in north London from Liverpool in 1996 and went on to have a difficult time with Spurs.
Scales suffered with numerous injury problems and struggled to nail down a place in the team. Few tears were shed when the three-time England international departed for Ipswich in 2000.
29. Benjamin Stambouli
Stambouli helped Montpellier win the Ligue 1 title in 2011/12, which was only his second season as a professional. Two years later he was on the move as Tottenham paid around £4.7m for the midfielder.
It looked like a bargain at the time, but it soon became clear that Montpellier had got the better end of the deal. Tottenham sold Stambouli to PSG after just a single season at White Hart Lane.
28. Kevin-Prince Boateng
Boateng went on to play for Borussia Dortmund, AC Milan and Barcelona, but no one could have expected that during his ill-fated Tottenham spell. Acquired from Hertha Berlin in 2007, Boateng penned a four-year deal at White Hart Lane.
He only lasted for half that time and made just 14 appearances in the Premier League, only half of which were starts.
27. Mido
Mido had a reasonably productive loan spell with Tottenham between January 2005 and the summer of 2006, scoring 13 goals in 36 Premier League games.
But things went south when Spurs made the deal permanent. The Egyptian only managed one top-flight goal in 2006/07, while Martin Jol slammed the striker as “irresponsible and disrespectful” due to his outspoken nature off the pitch.
26. Matt Doherty
Spurs parted with around £13.4m to land Doherty in the summer of 2020. The Irishman had performed well for Wolves over the last couple of seasons, in which he was virtually ever-present in the Premier League.
However, Doherty struggled to make the step up and he soon found himself as a bit-part player in north London. Tottenham terminated his contract in January 2023.
25. Jason Cundy
During his time at Tottenham, Cundy scored one of the most unusual goals in Premier League history, as a tackle near the halfway line flew into the net with the assistance of the wind.
That was the only highlight of his time at Spurs, which encompassed just 28 outings in the top flight between 1992 and 1996. The defender was never able to win over the Tottenham fans, perhaps in part due to his Chelsea connections.
24. Hossam Ghaly
Tottenham beat Arsenal to the signing of Ghaly in 2006/07, but the Gunners had the last laugh. The Egyptian wasn’t a total disaster on the field, although he didn’t exactly set the Premier League alight either.
Ghaly ultimately proved to be more trouble than he was worth, culminating in the midfielder throwing his shirt on the floor after being substituted against Blackburn. “I’m just so angry with myself,” he said later. So were Tottenham.
23. Paul Stalteri
A Bundesliga winner with Werder Bremen in 2004, Stalteri joined Tottenham the following year. The Canadian idolised Paolo Maldini while growing up, but unfortunately for Spurs there were no other connections between the pair.
Stalteri was the first-choice right-back in 2005/06, but he didn’t do enough to convince Spurs of his long-term worth. Pascal Chimbonda was signed as an upgrade, leaving Stalteri on the fringes of the squad.
22. Ramon Vega
Tottenham splashed out £3.75m on Vega in 1997 as Gerry Francis sought to bolster the team’s defence. But the Switzerland international had problems with his form and fitness almost from the start, severely hampering his chances of having a successful Spurs career.
Loaned to Celtic in 2000, Vega was released by Tottenham the following year. He went on to play for Watford in the second tier.
21. Clinton Njie
Lyon’s academy has produced numerous stars in the 21st century, and Tottenham thought they had snared one when they bought Njie in 2015. He struggled to get into the team, though, before suffering a serious knee injury in December.
Njie was back in France the very next season, joining Marseille on loan and then signing a permanent deal at the Stade Velodrome. All eight of his Premier League appearances were as a substitute.
20. Ricardo Rocha
A terrific performance against Barcelona icon Ronaldinho seemed to confirm that Rocha was ready to leave Benfica and move to one of Europe’s top five leagues. Tottenham won the race for his signature in 2007, but they soon wished they hadn’t.
The Portuguese defender made just 12 Premier League appearances for the north Londoners, as he struggled to adapt to the physical nature of the English game.
19. Bobby Mimms
Signed as the successor to Ray Clemence in 1988, Mimms was probably on a hiding to nothing at Tottenham. Even so, the goalkeeper made numerous mistakes in his debut season and he was eventually dropped by Terry Venables.
Mimms was unable to regain his place thereafter. He was loaned out to Aberdeen in 1990 before being permanently sold to Blackburn.
18. Vlad Chiriches
Tottenham used some of the money from selling Gareth Bale to Real Madrid to sign Chiriches, a decision about which the less said the better.
The central defender had been solid enough at Steaua Bucharest, but Romania’s Liga 1 is not quite as taxing as the Premier League. Chiriches was named man of the match on his debut, but there were few other highlights from his 43 games for Tottenham.
17. Bobby Zamora
Zamora was integral to Brighton’s rise from the fourth tier to the second in the early 2000s, prompting Tottenham to spend £1.5m to bring him to the capital. Hopes were high for the Englishman, but he fell well short of expectations.
Indeed, Zamora only managed one goal in 18 appearances for Spurs. He was out of the door within months, used as a makeweight in a deal which saw Jermain Defoe swap West Ham for Tottenham.
16. Jonathan Blondel
An unknown figure in England when he arrived in 2002, Blondel had just one season of senior football under his belt. That didn’t deter Tottenham, who thought they had unearthed a Belgian gem.
Spoiler alert: they hadn’t. Blondel simply wasn’t good enough, playing just twice in the Premier League before Spurs admitted their mistake. The midfielder went on to have a respectable career with Club Brugge.
15. David Jenkins
Jenkins began his career with Arsenal before jumping ship to Tottenham in 1968. He spent four years with the club but only ever made 14 league appearances, a statistic which shows how disappointing the forward was at White Hart Lane.
Jenkins notched only two goals in all competitions, but Spurs were unable to get rid of the former Arsenal man until 1972, when he joined Brentford.
14. Georges-Kevin Nkoudou
After establishing himself as a bright young talent at Marseille, Tottenham bought Nkoudou to the Premier League for £11m in 2016. He failed to force his way into the starting XI in his debut season but the future Cameroon international was expected to come good later.
He didn’t. Nkoudou flattered to deceive throughout his three years on Spurs’ books, which included loan spells at Burnley and Monaco. He was sold to Besiktas for just £4.6m in 2019.
13. Federico Fazio
A dependable performer for La Liga side Sevilla, Tottenham thought they would be bolstering their backline by buying Fazio in 2016. But the Argentine was sent off on his debut against Manchester City and things didn’t get much better from there.
He was sent off again on his seventh appearance for Spurs, and only made 25 more before returning to Sevilla. “England is different, there is not much tactical work,” he said later in an unconvincing attempt to absolve himself.
12. Gilberto
Daniel Levy sanctioned a deal for Gilberto on transfer deadline day in January 2008. The Brazilian was expected to become Tottenham’s go-to left-back, but he arrived injured and couldn’t make his debut for weeks.
When he did, Gilberto was taken off at half-time after a poor performance. He only played seven Premier League games before being asked to seek pastures new.
11. Vincent Janssen
Several strikers signed from the Eredivisie had flopped before Janssen, but Tottenham fans were nevertheless delighted to land a player who had scored 31 times for AZ in 2015/16. “He tick[s] all the boxes we need,” Mauricio Pochettino beamed.
Alas, it turned out to be £17m down the drain. Janssen scored only two Premier League goals in 31 matches, and he didn’t even get a chance when Harry Kane and Son Heung-min were unavailable in 2019.
10. David Bentley
Wondergoal against Arsenal aside, Bentley contributed little to the Tottenham cause during his five years under contract at White Hart Lane. The attacking midfielder wasn’t short of natural talent, but he failed to put that to good use.
A maverick on and off the pitch, Bentley retired before his 30th birthday after admitting that he had fallen out of love with football.
9. Sergiy Rebrov
Rebrov was a prolific striker for Dynamo Kyiv throughout the 1990s, with his goals firing the Ukrainian outfit to the latter stages of the Champions League in the final part of the decade. That paved the way for an £11m transfer to Tottenham at the turn of the century.
They should have saved their money. Rebrov made the net bulge only 15 times in 75 outings for Spurs, and just once in 30 Premier League matches in 2001/02.
8. Ilie Dumitrescu
A standout performer as Romania shone at the 1994 World Cup, Dumitrescu joined Tottenham for £2.6m - a significant sum at the time - later that summer. An Ossie Ardiles signing, the attacker failed to earn the trust of Gerry Francis, who took charge in November of that same year.
Dumitrescu was never able to salvage his Spurs career from there, and he was sold to West Ham in 1996.
7. Paulinho
After receiving £86m from the sale of Gareth Bale in 2013, Tottenham promptly turned wine into water. Of the seven signings the club made that summer, Paulinho was undoubtedly one of the biggest disappointments.
A box-to-box midfielder, the Brazilian looked ready-made for the Premier League. But Paulinho fell out of favour within 18 months and was sold to Guangzhou Evergrande in early 2015. To the shock of every Spurs supporter, he later played for Barcelona.
6. Paolo Tramezzani
The 1997/98 campaign was one of Tottenham’s worst in the Premier League era and they set about improving their squad the following summer. Among the arrivals was Tramezzani, a £1.5m purchase from Piacenza.
A fairer fee would have been £1.50. The Italian defender made only six league appearances for Spurs, who cut their losses by sending him back to Piacenza in 2000.
5. Grzegorz Rasiak
Eighteen goals for second-tier Derby in 2004/05 convinced Tottenham to make a move for Rasiak, who ended up costing them £3m. Alarm bells should have been ringing when Martin Jol described the incoming striker as an “honest player”, damning him with faint praise from the get-go.
Rasiak managed just eight goalless appearances in the Premier League before Spurs arranged his exit, initially on loan.
4. Bongani Khumalo
“He's not expensive and we've got a tie-up with the club, SuperSport United, so we've taken him on,” Harry Redknapp said of Khumalo, an introduction which didn’t exactly set pulses racing at White Hart Lane.
Just as well. Redknapp soon realised Khumalo wasn’t up to it, loaning him out to Preston within a couple of months. He never made a single senior appearance for Spurs.
3. Helder Postiga
After finding the back of the net 18 times for Porto in 2002/03, Postiga was a wanted man around Europe. With some justification, Tottenham felt they had pulled off a coup by securing his services.
Yet blue moons were more frequent that a Postiga goal for Spurs: he managed just one in 19 Premier League games and was back at Porto within a year.
2. Roberto Soldado
After selling Gareth Bale for £86m in 2013, Tottenham used the proceeds to sign seven new first-team players. The arrival of Soldado, who had just scored 24 goals in the 2012/13 La Liga campaign, generated the most excitement.
The Spaniard scored the winner on his debut, but that was as good as it ever got. A dry patch saw Soldado lose all confidence, and his Spurs career ended with a record of just 16 goals in 76 matches.
1. Tanguy Ndombele
After finishing as Champions League runners-up in 2019, Tottenham sought to regenerate their squad to go again under Mauricio Pochettino. Ndombele was the headline signing that summer, as Spurs broke their transfer record in a deal worth £55.5m.
But Pochettino left in the autumn and Ndombele didn’t impress his replacement, Jose Mourinho. His lacklustre displays saw him embark on loan moves elsewhere as consecutive Spurs managers didn’t take to the Frenchman.
