Tottenham's 10 greatest Premier League transfers ever

Analysis

FT Desk

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, FootballTransfers runs through the 10 best Tottenham signings of the Premier League era.

Teddy Sheringham - €3.2m (from Nottingham Forest, 1992)

Teddy Sheringham is regarded as one of Tottenham's best players of the Premier League era and he forged that reputation for himself across two successful stints at the club.

He originally arrived in north London from Nottingham Forest in 1992 and after 99 goals in 197 games, Sir Alex Ferguson had seen enough and paid €5.3m to sign him in 1997. After a successful stint at Manchester United, Sheringham returned to Spurs on a free transfer in 2001 and spent another two years at the club before joining Portsmouth.

A silky forward capable of creating as well as scoring, Sheringham found the back of the net a total of 125 times across his two spells at Tottenham and remains a huge fan's favourite.

Jurgen Klinsmann - €2.8m (from Monaco, 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.

Klinsmann scored 38 goals in just 68 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.

David Ginola - €2.9m (from Newcastle, 1997)

Sir Bobby Robson had wanted to sign David 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.

And, 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.

He spent just three years at Spurs, scoring 22 goals in 127 games, but he remains a cult hero to this day.

Gareth Bale - €14.7m (from Southampton, 2007)

Not the only player to leave Tottenham for Real Madrid, but quite possibly the most talented to ever represent Spurs in the Premier League era, Gareth Bale lit up the Premier League and Champions League across his six seasons 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.

He 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 he notably scored 21 goals in his final Premier League season. Real came knocking to the tune of €101m in 2013.

Returned briefly on loan in 2020, before seeing out his career with LAFC. In total, Bale scored 71 goals in 237 games across his two spells at Spurs.

Luka Modric - €22.5m (from Dinamo Zagreb, 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," Harry Redknapp once said about the Croatia legend. "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.

Jermain Defoe - €16.4m (from Portsmouth, 2009)

Jermain Defoe enjoyed two successful stints at Tottenham, with his first coming from 2004 until 2008, when he made a move to Portsmouth under Harry Redknapp.

However, just nine months after his move to Fratton Park, Redknapp left the club to join Spurs. Shortly afterwards, having spent only 12 months at Portsmouth, Defoe returned to Tottenham to reunite with his former manager and he immediately became Spurs' first-choice striker.

Defoe netted 18 Premier League goals during his first full season back at White Hart Lane and he helped the club establish themselves as regular Champions League challengers under Redknapp. In total, he scored 143 goals across his two spells at Spurs, before leaving for good in 2014.

Hugo Lloris - €12.6m (from Lyon, 2012)

A France international when they signed him, Hugo Lloris arrived from Lyon in 2012 for a relative snip at just €12.6m. A total of 151 clean sheets in 447 games later, he left the club in 2024 as one of the best goalkeepers of the modern Premier League era.

Lloris, like most Spurs signings in the 21st century, failed to win a single trophy during his stint at the club, but the Frenchman remains one of their best ever signings and he was named club captain after just two seasons in north London.

After 12 years at the club, Lloris left Spurs to join MLS side LAFC on a free transfer.

Christian Eriksen - €14.2m (from Ajax, 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 €14.2m when they bought him in 2013, reuniting with former Ajax team-mate Jan Vertonghen.

Eriksen was twice named the club's Player of the Year before leaving for Inter Milan in January 2020, while he notched over 150 goal involvements in 305 games for Spurs.

Dele Alli - €6.6m (from MK Dons, 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. He formed an immense attacking unit with Harry Kane and the aforementioned Eriksen under Mauricio Pochettino, becoming one of the best players in the English top flight.

His career unfortunately tailed off in the 2020s due to a combination of injuries and personal issues, but he remains one of Spurs' best signings in recent memory.

Son Heung-min - €30m (from Bayer Leverkusen, 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 north 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 in his final game for the club.

In total, Son netted 173 times in 454 games during an illustrious decade at Spurs.