Eberechi Eze’s move to Arsenal came after the former Crystal Palace star looked so close to joining Tottenham Hotspur.
As embarrassing as it is for the Lilywhites to lose out to their north London rivals in this manner, it is by no means the first time they have been bested in the transfer market.
Indeed, Spurs have had some humiliating episodes over the years when it comes to securing their transfer targets, with some players all but certain to seal a switch to N17 before it all went wrong.
In this list, we’ve ranked Tottenham’s biggest fumbles in the transfer market.
Ranking factors
To put these players in order, we have considered the following criteria:
- Progress made in a transfer – how late Spurs got into the signing process before the plug was pulled
- Reason for failure – whether the reason they missed out on a player was in their control or embarrassing
- What might have happened – the potential effect of signing the player they missed out on
11: Sergio Aguero (2011)
Spurs met his release clause
It’s important to point out that not all of these close calls are Tottenham’s fault. One such case would be when they sought the services of Atletico Madrid’s Sergio Aguero, even matching his £38m release clause.
According to The Guardian, this did not mean that the La Liga giants had to sell up, with the Argentinian eventually signing for Manchester City the following summer.
Given that the striker ended his career with 184 Premier League goals, he is almost certainly a regrettable miss.
10: David Villa (2013)
CL winner on verge of joining until Atletico hijack
Atletico Madrid appeared to have it in for Spurs, as they foiled the Lilywhites’ chances of recruiting David Villa from Barcelona in 2013.
Spurs’ £8m offer looked set to entice the Spaniard to the Premier League, but he opted to stay in Spain for almost half the price.
Atleti went on to win the title in his first season, so Villa can look back on his decision fondly.
9: Bruno Fernandes (2019)
Levy failed to meet Sporting’s demands
It’s unclear whether Tottenham failed to stump up the cash or refused to be messed around in their failed pursuit of Bruno Fernandes, with the Lilywhites seemingly close to a deal before the Portugal international’s eventual move to Manchester United.
In summer 2019, it was thought that Sporting CP were set to accept Spurs’ proposal before having a change of heart and demanding more money – twice as much, according to BBC Sport.
Levy never returned with an improved bid and Sporting made other plans, selling Raphinha to leave Bruno Fernandes stuck in Portugal for another six months.
8: Eden Hazard (2012)
Failure to make Champions League saw Belgian choose Chelsea
On one hand, Spurs’ on-pitch shortcomings were at fault as they missed out on Eden Hazard.
But the circumstances under which they didn’t qualify for the Champions League will arguably leave a bitter taste in the mouth, especially given it appears to have helped the Belgian winger opt for Chelsea in 2012.
In any other season, Spurs would have qualified for the Champions League via their fourth-place finish in 2011/12, but with Champions League winners Chelsea finishing sixth, they took Tottenham’s berth.
Hazard would later claim that choosing his next destination after leaving Lille was then much easier.
To make matters worse, Hazard scored the goal that killed off Tottenham’s title challenge in 2016.
7: Paulo Dybala (2019)
Image rights drama scuppered summer coup from Juventus
Of all the reasons on this list that transfer negotiations turned sour, this has to be the most bizarre.
As part of any deal to sign Paulo Dybala in 2019, Spurs would have had to agree on a settlement with the Malta-based company that held the Argentinian’s image rights.
Some reports had claimed this fee could cost £40m alone, while Spurs were also hamstrung by the Premier League’s early closing of the summer window, with other European clubs having more weeks to conclude business.
In the end, they ran out of time after failing to tie up all the loose ends.
6: Eberechi Eze (2025)
Tottenham signing wrecked by 11th-hour Arsenal approach
Everything was going swimmingly for Spurs, who were hoping to build on a positive start to Thomas Frank’s reign by swooping for FA Cup final match-winner Eberechi Eze from Crystal Palace.
It was no secret that Arsenal were previously keen on the attacker, though things had gone cold as Spurs made progress with their own deal.
But before the ex-Palace star signed on the dotted line, a late plea to Mikel Arteta saw Arsenal reignite their interest, putting everything with Spurs on ice.
Eze had been snatched from right under their noses and was paraded in front of the Gunners fans less than 72 hours later.
5: Luis Diaz (2022)
Hesitation allowed Liverpool to swoop in
Daniel Levy apparently dropped the ball on Spurs’ approach for Luis Diaz in 2022, despite appearing willing to put forward a £46m package.
But their dallying left the door open for Liverpool – an understandably more attractive destination, in fairness – to swoop for the Colombian.
However, given that Diaz signed for a little more than Spurs’ would-be offer, a bit more urgency could have made all the difference.
Diaz went on to secure every domestic trophy during his time at Anfield.
4: Jack Grealish (2016)
Levy horrendously lowballed Villa out of doing a deal
Spurs sensed an opportunity when promising starlet Jack Grealish was relegated from the Premier League with Aston Villa in 2016.
But Tottenham failed to read the room and meet Villa’s – and Jack’s father’s – valuation, with all other parties keen for the Villans to recoup a sizeable fee.
Grealish, who would eventually move for £100m in 2021, was the subject of derisory offers of around £8m and £12m, before a final offer of £25m was also considered sub-par. What could have been…
3: Joao Moutinho (2012)
Fee agreed & contract signed… but ran out of time
In terms of being able to formally announce a signing, no one on this list came as close as Joao Moutinho did back in 2012.
The parties had agreed on a fee of around £24m, with Moutinho even travelling to London and signing a contract – only for the transfer deadline to deny Tottenham a significant coup.
Unfortunately for Spurs, the paperwork did not reach the Premier League in time, with Moutinho himself claiming he was “one minute away” from becoming a Spurs player. Ouch.
2: Emmanuel Petit (1997)
Tottenham famously paid for Frenchman’s cab to Arsenal
It’s almost a tale as old as time, but few things have come close to rivalling the humiliation of not only missing out on Emmanuel Petit, but also footing the bill for his subsequently successful talks with rivals Arsenal.
It certainly turned out to be a wise decision from the midfielder, who capped a superb first campaign in which he won the double by scoring in the World Cup final for France.
Who knows how he may have transformed Tottenham’s fortunes in a parallel universe, even if the Frenchman would later claim that Arsenal were prepared to pay him substantially more than their north London counterparts.
1: Willian (2013)
Completed Spurs medical before late Chelsea bid
Tottenham looked to have done all the hard work as they had virtually sealed a move for Willian from Russian outfit Anzhi Makhachkala.
With the Brazilian completing a Spurs medical, it was surely only a matter of time before he’d be holding up a Tottenham shirt.
But a late Chelsea offer – apparently instigated by former owner Roman Abramovich – superseded Tottenham’s progress, with the west Londoners somehow managing to push ahead in the race for his signature.
Daniel Levy was described as “incandescent” following the Blues’ sudden approach, with there being some animosity between the two football club owners. Willian would end up making London a second home, having flourished at Chelsea and Fulham, winning plenty of trophies at Stamford Bridge.
Spurs will have been left reeling with their inability to get a deal over the line, but he was just one of many that got away.
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