Tottenham’s top ten biggest transfer sales of all-time – From Trippier to Harry Kane

While Tottenham Hotspur may not have lifted a trophy since the 2007-08 EFL Cup, the club has frequently been at the centre of blockbuster transfers, with some of their most talented players fetching staggering sums and leaving fans wondering what could have been. Let’s take a look through Tottenham’s top ten biggest transfer sales of all-time.

Tottenham’s trophy drought and talent exodus

For a club that has long prided itself on nurturing some of the game’s finest talents, Tottenham Hotspur have endured a painful wait for silverware, with their last major honour arriving over 15 years ago.

The lack of trophies has often seen the club’s brightest stars depart in search of glory elsewhere, and many of them found exactly that after leaving north London.

From Gareth Bale’s record-breaking move to Real Madrid to Harry Kane’s recent high-profile transfer to Bayern Munich, Spurs have been no strangers to lucrative sales, with each departure stirring mixed emotions among their devoted fanbase.

The funds generated by these sales have occasionally been reinvested well but have often sparked debates over whether the club has made the most of their financial windfalls.

Despite the frustrations, Tottenham’s knack for commanding hefty fees for their departing players is a testament to the talent they have cultivated over the years.

Here, we delve into Tottenham’s top ten biggest transfer sales in the club’s history and explore the details of these headline-grabbing transfers.

Tottenham’s top ten biggest transfer sales of all time

10. Kieran Trippier – £18.7 million

• To: Atletico Madrid
• Date: 17 July 2019
• Age at the time: 28
• Spurs appearances: 114
• Spurs goals: 2
• Honours at Spurs: None
• Signed for: £3.5 million

Signed from Burnley for just £3.5 million in 2015, Kieran Trippier quickly established himself as a dependable right-back, renowned for his pinpoint crossing and set-piece ability. His move to Atletico Madrid in 2019 was met with some surprise, yet the Englishman thrived in Spain, helping Atletico secure the La Liga title in 2020-21.

9. Robbie Keane – £20.4 million

• To: Liverpool
• Date: 28 July 2008
• Age at the time: 28
• Tottenham appearances: 306
• Tottenham goals: 122
• Honours at Tottenham: EFL Cup (2007-08)
• Signed for: £12 million

Robbie Keane’s transfer to Liverpool in 2008 brought an end to a remarkable first spell at Tottenham, where the Irish striker etched his name into club folklore. Although his time at Anfield was underwhelming, Keane made a swift return to Spurs for a fee that underscored his enduring value.

8. Christian Eriksen – £23 million

• To: Inter Milan
• Date: 28 January 2020
• Age at the time: 27
• Tottenham appearances: 305
• Tottenham goals: 69
• Honours at Tottenham: None
• Signed for: £11 million

Signed for £11 million in 2013, Christian Eriksen proved to be a creative maestro during his time at Spurs, twice earning the club’s Player of the Year award. Despite his departure to Inter Milan in 2020, Eriksen’s legacy at Tottenham remains untarnished, with his contributions pivotal in their journey to the 2019 UEFA Champions League final.

7. Michael Carrick – £23.1 million

• To: Manchester United
• Date: 31 July 2006
• Age at the time: 25
• Spurs appearances: 75
• Spurs goals: 2
• Spurs at Tottenham: None
• Signed for: £3.5 million

Michael Carrick’s move to Manchester United in 2006 marked the end of a brief yet impactful spell at Tottenham. The deep-lying playmaker’s calmness on the ball and tactical awareness made him a prized asset, and his subsequent success at Old Trafford only highlighted what Spurs had lost. At least Tottenham managed to get a good price at the time for a player who to this day remains in the club’s top ten biggest transfer sales of all-time

6. Steven Bergwijn – £26.6 million

• To: Ajax
• Date: 8 July 2022
• Age at the time: 24
• Spurs appearances: 83
• Spurs goals: 8
• Honours at Spurs: None
• Signed for: £25m

After joining Tottenham from PSV Eindhoven in January 2020, Steven Bergwijn dazzled with moments of brilliance but struggled for consistency. His return to the Netherlands with Ajax proved to be a lucrative deal for Spurs, albeit a bittersweet farewell for fans who saw glimpses of his potential.

5. Luka Modric – £29.8 million

• To: Real Madrid
• Date: 27 August 2012
• Age at the time: 26
• Spurs appearances: 160
• Spurs goals: 17
• Honours at Spurs: None
• Signed for: £16.5 million

Luka Modric’s transfer to Real Madrid was the beginning of an illustrious chapter for the Croatian midfielder. Though Spurs failed to claim silverware during his tenure, Modric’s elegance and vision on the pitch made him a fan favourite, and his subsequent Ballon d’Or win validated his greatness.

4. Dimitar Berbatov – £32.3 million

• To: Manchester United
• Date: 1 September 2008
• Age at the time: 27
• Tottenham appearances: 102
• Tottenham goals: 46
• Honours at Tottenham: EFL Cup (2007-08)
• Signed for: £16 million

The enigmatic Bulgarian forward became a household name at Spurs with his flair and clinical finishing. While his move to Manchester United broke hearts, Berbatov left behind fond memories of his spellbinding performances in a Spurs shirt.

3. Kyle Walker – £44.8 million

• To: Manchester City
• Date: 14 July 2017
• Age at the time: 27
• Tottenham appearances: 229
• Tottenham goals: 4
• Honours at Tottenham: None
• Signed for: £9 million

Kyle Walker’s transfer to Manchester City in 2017 made him the world’s most expensive defender at the time, underlining his rise to prominence as one of the Premier League’s finest right-backs. Not only is he in Tottenham’s top ten biggest transfer sales of all-time, but he is also the biggest defender sale in the club’s history.

2. Harry Kane – £80.8 million

• To: Bayern Munich
• Date: 12 August 2023
• Age at the time: 30
• Tottenham appearances: 435
• Tottenham goals: 280
• Honours at Tottenham: None
• Signed for: Academy graduate

Harry Kane’s departure to Bayern Munich was a defining moment for Spurs, ending an era where the academy graduate had carried the team on his shoulders, becoming the club’s all-time top scorer. Kane scored 280 goals and laid on another 61 assists in 435 games for Spurs (TransferMarkt).

1. Gareth Bale – £85.9 million

• To: Real Madrid
• Date: 1 September 2013
• Age at the time: 24
• Tottenham appearances: 237
• Tottenham goals: 71
• Honours at Tottenham: EFL Cup (2007-08)
• Signed for: £13m

Number one on Tottenham’s list of top ten biggest transfer sales of all-time, Gareth Bale’s move to Real Madrid shattered records and ushered him into a world of galacticos. The Welshman’s electrifying performances in his final Spurs season remain unforgettable, with his name etched into club folklore.

A club of sellers or strategic rebuilders?

The Lilywhites’ top sales tell a tale of shifting strategies and ambitions over the years. While it is undeniable that Spurs have lost some generational talents, these sales also highlight the club’s emphasis on financial prudence and reinvestment. Whether these funds have been effectively utilised, however, is a question that has long divided fans and analysts.

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