Tottenham's 10 best transfers of all time

FT Desk

• Updated: 14 Mar 2026 14:18 CDT
• 8 min read

Analysis

Tottenham Hotspur under Daniel Levy developed a reputation for being hard-nosed in transfer negotiations, often buying low and selling high.

But from Jurgen Klinsmann to Gareth Bale, some of the best players in the world have graced White Hart Lane.

Spurs even got to the Champions League final under Mauricio Pochettino in 2019, where a team featuring more of their best-ever acquisitions, such as Son Heung-min, were beaten by Liverpool in an all-English final.

With Levy sacked after a quarter of a century in charge of transfers, the jury is still out on whether Spurs can find that magic touch again that helped them establish themselves among the Premier League's elite.

Below, Football Transfers looks at Tottenham's 10 best transfers of the Premier League era…

Lucas Moura - from PSG for €28m in 2018

Lucas Moura joined Tottenham from Paris Saint-Germain in January 2018, and unlike so many winter arrivals, hit the ground running at White Hart Lane, scoring on his first start, against Rochdale in the FA Cup.

Often accused of being inconsistent in subsequent seasons, the Brazilian nonetheless went down in Lilywhites folklore after firing Spurs into their first Champions League final in 2019. Ajax were leading their semi 2-0 until a Moura hat-trick, which he completed with the final kick of the ball in the 96th minute.

David Ginola - from Newcastle for £2.5 million (€2.8m) in 1997

Sir Bobby Robson had wanted to sign Ginola for Barcelona the season before he swapped Newcastle for Tottenham, but when Kevin Keegan left Tyneside in January 1997, some of his favourites, like Ginola and Les Ferdinand, soon followed him out the door.

Tottenham arguably got the best of Ginola. The French wing wizard was the PFA Players' Player of the Year and the FWA Footballer of the Year in 1999, becoming the first player ever to win the awards whilst playing for a club that didn't finish in that year's top four.

Hugo Lloris - from Lyon for €15m in 2012

A France international when they signed him, Lloris arrived from Lyon in 2012 for a relative snip at €15m. A total of 151 clean sheets in 508 games later, he left the club in 2024 as one of the best goalkeepers of the modern Premier League era.

Lyon inserted a 20 per cent sell-on clause into his contract, but they never managed to get more than the initial €15m. Lloris joined MLS side LAFC on a free transfer after 12 years at Spurs.

Christian Eriksen - from Ajax for €12.5m in 2013

One Tottenham fan took to social media to burn his jersey when Christian Eriksen signed for Manchester United on a free transfer from Brentford in 2022, but he is rightly remembered fondly by most Spurs fans.

A creative genius, Eriksen only cost Tottenham €12.5m when they bought him in 2013, reuniting with former Ajax teammate Jan Vertonghen. Eriksen was twice named the club's Player of the Year before leaving for Inter Milan in January 2020.

Dele Alli - from MK Dons for £5m (€5.6m) in 2015

It's easy to forget that Dele Alli was once one of the brightest prospects in English football, and Tottenham deserved immense credit for plucking him from relative obscurity with MK Dons in 2015.

A scorer of great goals and, in his 2016/17 pomp, a great scorer of goals with 18 in the Premier League - from midfield - Alli was also an England regular until 2019.

However, his lack of application later left managers from Jose Mourinho to Antonio Conte at a loss. His career went downhill in the 2020s, even going several years without playing a competitive fixtures due to a combination of injuries and personal issues.

Paul Gascoigne - from Newcastle for £2.2 million (€2.5m) in 1988

Ok, we may have to dip back to just before the Premier League era for this one, but Paul Gascoigne did at least play in the Premier League for Tottenham (apologies, Dave Mackay).

But Gazza was at his electric best for Spurs, having joined them from Newcastle at Manchester United's expense in 1988. "He promised to sign for us, and I went on holiday," Sir Alex Ferguson later recounted. "I got a phone call from Martin Edwards saying he'd signed for Tottenham because they bought his mother a house for £80,000 and, dearie me, I couldn't believe it."

Injured his own knee with a reckless challenge on Gary Charles in the 1991 FA Cup final before joining Lazio for €6.2m (equivalent to over €10m today) in 1992. Football Italia on Channel 4 was started largely to follow his progress, and he subsequently enjoyed a second peak with Rangers.

Luka Modric - from Dinamo Zagreb for €18.5m in 2008

Luka Modric blossomed into arguably the best midfielder in the world at Real Madrid, and he was the first player not named Cristiano Ronaldo or Lionel Messi in 10 years to be awarded the Ballon d'Or when he won it in 2018.

But it shouldn't be forgotten that Modric was also a world-class operator in his four years with Tottenham. He arrived as the first of 11 summer signings under Juande Ramos in the summer of 2008, but soon outstripped the others.

"He's a hell of a player and a manager's dream," effused Ramos successor as manager, Harry Redknapp. "He trains like a demon and never complains, will work with and without the ball on the field and can beat a defender with a trick or with a pass. He could get into any team in the top four."

It turned out Modric could get into the top one in world football. He won six Champions Leagues after his €35m switch to Madrid, before joining Italian giants AC Milan at the age of 39.

Jurgen Klinsmann - from Monaco for €2.2m in 1994

Spurs have had world-class operators before and since Jurgen Klinsmann, but the West Germany World Cup winner's arrival from Monaco in 1994 arguably secured Tottenham's reputation as a viable destination for top players in the early Premier League era.

Renowned as a cheat in England, he immediately won fans over on his debut, scoring a headed winner against Sheffield Wednesday and immediately celebrating with a diving celebration that has been copied far and wide since.

Scored 38 goals in 66 games, sold over 150,000 shirts with his name emblazoned on the back, was inducted into Madame Tussauds Wax Museum and still enjoys cult status among Spurs fans today.

Gareth Bale - from Southampton for £10 (€11.8m in 2007)

Not the first player to leave Tottenham for Real Madrid, but quite possibly the most talented to represent Tottenham in the Premier League era, Bale lit up the Premier League and Champions League across his first six season at White Hart Lane.

It's incredible to think that the Welsh wing wonder was signed from Southampton as a left-back in 2007, and the early headlines weren't kind, with Spurs winless in Bale's first nine games for the club. But he soon turned things around, and after being moved into a more attacking role by Harry Redknapp, he never looked back.

Obliterated Maicon - the Brazilian at the time regarded as one of the best right-backs in the world - when Tottenham beat Inter Milan 3-1 in the 2010/11 Champions League group stage, and Real came knocking to the tune of €100m in 2013.

Returned briefly on loan in 2020, before seeing out his career with LAFC.

Son Heung-min - from Bayer Leverkusen for €30m in 2015

Modric and Bale may have Champions League trophies that eluded Son Heung-min, but the South Korean spent the prime of his career in Nort London, and his ceiling proved to be extremely high indeed.

Making a mockery of the notion of a "Bundesliga tax" following his €30m arrival from Bayer Leverkusen in 2015, Son became one of the best attackers of the past decade, forming a formidable partnership with No.9 Harry Kane.

Son is widely regarded as the greatest South Korean, if not the greatest Asian, player of all time. Before leaving in 2025 - also for LAFC - he even managed to end Spurs' trophyless curse by captaining the side to the Europa League title.

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