Tottenham Hotspur have pulled off some eye-catching signings in their history, with Daniel Levy spending big in recent times.

However, Spurs have also missed out on bringing some world-class players to north London, with Eberechi Eze the latest Tottenham transfer to fall through. With a deal close to being finalised, fierce rivals Arsenal swept in and poached the attacking midfielder frim under Spurs’ nose.

Unfortunately, it hasn’t been just Eze. Tottenham have been pipped to the post or rejected by a plethora of legends, from Cristiano Ronaldo to Kylian Mbappe.

Tottenham's most expensive signings of all time

A detailed look at Spurs’ 10 most expensive signings of all time.

ByCharlie Smith 10 superstars Tottenham Hotspur nearly signed 10 Cristiano Ronaldo

Former Tottenham scout and player Ronny Rosenthal was urging the Spurs to sign Cristiano Ronaldo when he was coming through at Sporting CP.

However, Spurs didn’t listen, with Manchester United landing the Portuguese superstar for just over £12m in 2003.

9 Kylian Mbappe

Back in 2015, a teenage forward by the name of Kylian Mbappe impressed Spurs chiefs for Monaco during a Europa League clash against Tottenham.

Those in north London kept tabs on the Frenchman and were looking to bring him to the club, however, they quickly realised he was out of reach, with Mbappe instead choosing PSG.

8 Diego Maradona

Tottenham legend Teddy Sheringham had two spells with Spurs and once revealed that the club were in talks to sign Diego Maradona.

Ossie Ardiles managed Spurs in 1993-1994 and once told Sheringham he was looking to partner him in attack with Maradona.

7 Rivaldo

Levy missed out on signing Brazilian icon Rivaldo in 2002 when he was on the search for a new club after leaving Barcelona.

Manuel Auset, Rivaldo’s friend and lawyer, said that Spurs offered the then-30-year-old a move to the Premier League, but he instead chose AC Milan.

6 Eden Hazard

Now remembered as a Chelsea legend, Eden Hazard could quite easily have been a Tottenham player when leaving Lille in 2012.

Former Spurs coach Clive Allen admitted that the Belgian star was “keen to come to Tottenham” but instead chose to head to Stamford Bridge.

5 Bruno Fernandes

Mauricio Pochettino and Tottenham made a concrete effort to sign Bruno Fernandes from Sporting CP in 2019.

Fernandes, who eventually moved to England with Man Utd, once revealed he was “really angry” his move to Spurs fell through after being convinced to join by Pochettino.

4 Sadio Mane

Tottenham and Pochettino made Sadio Mane their top target in 2016, however, Spurs were outbid by Liverpool.

The Reds paid £34m for Mane who’d go on to become an Anfield legend, with Tottenham instead using the money that would have gone on the forward for midfielder Moussa Sissoko.

Wins

9

Draws

5

Losses

2

Goals

3

Assists

2

3 Virgil van Dijk

Tottenham had Virgil van Dijk on their shortlist of central defender targets back in 2015 when the Dutchman was still on the books of Celtic.

Instead of signing Van Dijk, though, Spurs brought in Toby Alderweireld from Atletico Madrid, with Van Dijk signing for Southampton the same year.

2 Jack Grealish

At one point, Tottenham thought they were on course to sign Jack Grealish from Aston Villa for just £25m.

Grealish wasn’t happy about the failed transfer to Spurs in 2018, however, three years later, he’d cost Manchester City a then-British record £100m.

1 Luis Diaz

Tottenham were in pole position and pushing to sign Luis Diaz from FC Porto in the 2022 January transfer window before Liverpool hijacked a transfer.

The Reds paid a guaranteed fee of £37.5m for the Colombia international, who would go on to win the Premier League at Anfield before being sold for a profit to Bayern Munich.