The phrase “Tottenham Hotspur are interested in X player but may be perturbed by the asking price” is one that most, if not all, Spurs fans have grown accustomed to. While it always hasn’t been purely financial reasons, just how many quality players have slipped through the cracks for the Lilywhites? Find out with this best 11.
Spurs Best 11: The Ones That Got Away
Watch: How Tottenham replaced Harry Kane’s output
Goalkeeper: David Raya
Starting with a relatively fresh one, they reportedly missed out on the signing of Spanish goalkeeper David Raya in the summer transfer window. It should be said that the feeling is one of relief on this miss as the player signed instead, Guglielmo Vicario, has hit the ground running and is adored by fans.
Left back: Timothy Castagne
Slim pickings at LB as there have not been many LBs linked with Spurs, who of course have signed Ryan Sessegnon, Sergio Reguilon and the brilliant Destiny Udogie in the last 4 years alone. However, in 2020, Timothy Castagne was heavily linked with a move to London before he joined Leicester.
Center Backs: Milan Skriniar and Alessandro Bastoni
Our fictional CB pairing was also a Scudetto-winning one! In 2022, Antonio Conte, then manager of Tottenham wanted a new central defender and Bastoni was at the top of his list. In true Lilywhites fashion, a deal was unable to be completed and Conte was given an out-of-form Clement Lenglet on loan instead. In 2020, Jose Mourinho wanted Milan Skriniar and sent then Head of Recruitment, Steve Hitch to Italy to get a deal done for the CB. All Hitchen returned with were airport chocolates and Mourinho had to make do with Joe Rodon instead.
Right back: Ricardo Pereira
Back to Leicester City for a player who almost signed by Spurs. Periera was scouted to replace the outgoing Kyle Walker. However, in standard fashion, thumbs were twiddled, dillies were dallied, and nothing was done.
Central Midfielders: Joao Moutinho and Jack Grealish
Both these deals looked so close to being completed, only for the North London side’s haggling to get in the way. Moutinho was heavily linked throughout his career, but the signing seemed to be completed on deadline day in 2012, only for it to not be. In 2018, Grealish who was still at Aston Villa had reportedly even told his teammates goodbye only for the 25m deal to fall through at the last minute.
Central Attacking Midfielder: Paulo Dybala
This is the part of the XI where the quality truly shines. In 2019, on the back of reaching their first-ever CL final, The Lilywhites were close to agreeing a deal for Argentine attacker Dybala. A transfer fee and personal terms were already agreed only for the player’s image rights to be the stumbling block.
Left Wing: Sadio Mane
The man who won a penalty for Liverpool in that CL final against Tottenham, Mane was heavily linked with the Londoners while he was at Southampton. Then-boss Mauricio Pochettino was keen to work with the Senegalese only for his wage demands to be deemed too steep by the hierarchy. Like many on this list, Mane would instead join another team and go on to win the lot.
Right Wing: Luis Diaz
Take the Mane saga and add a couple of years and you have this. In January 2022, Luis Diaz was courted by Tottenham who looked all but sure to sign the player. Liverpool were looking to sign him in the summer window of 2022, but due to rival interest in January, they coughed up the funds needed to complete the signing as Spurs hesitated with the fee.
Center Forward: Leandro Damiao
Leandro Damiao and Tottenham Hotspur, a tale as old as time. In the early 2010s, there was no transfer in world football that seemed as inevitable as this one. The Lilywhites were in need of a striker and Damiao fit the bill and ticked all the boxes. For one reason or another (probably money), the deal never got over the line.
While Spurs have started well in the Premier League, their ambition will be tested in the upcoming transfer window as their squad does need some depth if they are to truly go all the way.