Top 10 BEST Tottenham signings of the Premier League era – Modric 3rd; fallen star 7th

Tottenham Hotspur have made some truly memorable signings during the Premier League era, and TEAMtalk has done a deep dive and ranked the top 10.

Going back to the very early days of snapping up Teddy Sheringham during the inaugural Premier League season to the later captures of the likes of Christian Eriksen and Son Heung-min, the club have been synonymous with attracting top attack-minded players to north London.

Last week, we looked at the 10 biggest stinkers signed by Spurs in the Premier League era.

But we’re not all about the doom and gloom, as here we have ranked the top 10 signings snapped up by Spurs over the last 30-plus years, and it’s no great surprise that the attacking third is where the majority of that focus lies (although not just yet)…

10) Jan Vertonghen

In a list that is dominated by brilliant attacking players, it’s important to recognise that Spurs did also sign some top defensive talent too – although Vertonghen is the only one that makes this list.

Signed from Dutch giants Ajax for just £9.6million (€12m) in 2012, Vertonghen went on to make 315 appearances for the club in all competitions and was a real mainstay of Mauricio Pochettino’s backline.

Indeed, at a time when Tottenham were challenging for the Premier League title under the Argentine, Vertonghen and Toby Alderweireld formed what was arguably the best centre-back pairing in English football.

A class act on and off the field, Vertonghen left Spurs in 2020 as a free agent, joining Benfica, and retired in 2025 after a stint back in his homeland at Anderlecht.

9) David Ginola

The French wing wizard only spent three seasons in north London, but his impact was spectacular during that time.

Signed from Newcastle in 1997 for just £2.5m, Ginola became an icon at White Hart Lane and was the first Tottenham player in the Premier League era to win the PFA Players’ Player of the Year award in 1999.

Ginola also won the League Cup during his time at Spurs and was inducted into the club’s Hall of Fame in December 2008. He was definitely ‘worth it’.

8) Teddy Sheringham

Arriving as a club-record £2.1m signing in 1992, the former England forward was sensational during his first four seasons in north London, scoring 90 goals in all competitions.

Renowned for having one of the best footballing brains in the game, Sheringham also notched 26 times in 80 appearances when he returned to the club in 2001 after four seasons at Manchester United.

Sheringham was still playing in the Football League in his early 40s, chalking up over 900 senior appearances during his club career, but it was at Tottenham where he emerged as one of the best strikers in the Premier League.

7) Dele Alli

In terms of value for money signings in the Premier League era, there are not many better than Dele Alli, who was signed for an initial £5m from MK Dons during the 2015 winter window.

Dele became such a huge player under Pochettino, forming part of an explosive attacking quartet alongside Harry Kane, Son Heung-min and Christian Eriksen.

He scored 67 goals and also chalked up 59 assists in 269 games in all comps before his career sadly fell off the rails.

6) Robbie Keane

Another club legend who previously admitted that the best spell of his career came during his first stint at Spurs between 2002-08.

Signed for £7m from Leeds United just before the transfer deadline in 2002/03, Keane chalked up 122 goals in 306 games in two stints in north London, winning the League Cup in 2008.

Keane also won the club’s Player of the Year award three times and was strongly tipped to take over as manager during last season’s relegation scrap before Roberto De Zerbi’s arrival.

It does, however, feel inevitable that he will one day be in charge at his spiritual home.

5) Jurgen Klinsmann

In terms of an overall impact signing during the early Premier League era, there were few bigger than the splash Tottenham made to bring the renowned striker to north London in 1994, following a World Cup in which he scored five goals for his country.

Spurs spent £2m to snap up the Germany international from Monaco, and he made an immediate mockery of his reputation as a ‘diver’ when he celebrated a debut goal against Sheffield Wednesday by flying through the air and landing a huge belly-flop.

Klinsmann won the Football Writers’ Association Footballer of the Year in his first and only full season at Tottenham, although he did return on loan late in the 1997/98 campaign, scoring nine goals in 15 games to save the club from relegation.

4) Christian Eriksen

The Danish legend was the one good thing to come out of the sale of Gareth Bale to Real Madrid, with Eriksen one of seven signings made by the club in the summer of 2013 – although we’ll give a little shout out to Erik Lamela too.

Snapped up for just £11m from Ajax, Eriksen went on to produce a combined 157 goals/assists in 305 outings for the club before leaving to join Inter Milan in 2020.

His playmaking ability behind the forward power of Harry Kane and Son Heung-min played a pivotal role during the Pochettino era and he rightly goes down as a club legend.

3) Luka Modric

Eyebrows were raised when Spurs snapped up the lightweight Croat from Dinamo Zagreb for £16.5m after he made a huge impression at the 2008 Euros.

He did struggle with the physical side of the English game initially before his technical wizardry really came to the fore under Harry Redknapp’s management.

Modric had the ability to completely dominate games from the centre of the park at Tottenham, despite his diminutive frame, and has gone on to have an incredible career.

Indeed, he is the only former Tottenham player to have won the Ballon d’Or, as he did with Real Madrid in 2018. He is even still playing at AC Milan now, at the grand old age of 41!

2) Gareth Bale

A spectacular time in north London that started with a curse and ended with an £85m sale to Real Madrid, Bale scored some of the most memorable goals in Tottenham’s Premier League history.

It was 24 league outings that Bale featured in without a Spurs victory at the start of his spell at the club, before that curse was finally broken in 2009. After that, the converted left-back went on the rampage as a he destroyed right-backs up and down the country.

Moving into more of a central role late in his time at Tottenham, goalkeepers had no answer to some of the best left-footed strikes from distance that the English top-flight has witnessed over the last 34 years.

A return on loan followed in 2020/21, but it wasn’t quite the same. That being said, Bale goes down as an absolute club legend and one remembered for completely changing the narrative of his career in spectacular fashion.

1) Son Heung-min

Speaking about legendary signings of the Premier League era, that brings us to the clear No.1 and one of the most loved Tottenham players of any era in north London – Sonny.

Signed for just £22m in the summer of 2015, the South Korean went on to chalk up 173 goals and 101 assists in 454 games in all competitions. Son is second on the all-time list of Premier League scorers for the club and fifth overall.

Son and Harry Kane formed the most prolific goal-combining duo in Premier League history, connecting for 47 goals before the latter left for Bayern Munich in 2023.

A sure sign of how much he is missed has been the complete lack of productivity from the left flank after he joined Los Angeles FC in the summer of 2025.

Note: Honourable mentions must also go to the likes of Dimitar Berbatov, Jermain Defoe, Hugo Lloris, Mousa Dembele, Rafael van der Vaart and Kyle Walker – and we could have named many more.