Amid their painful trophyless streak stretching all the way back to the 2007-08 season, Tottenham Hotspur have unsurprisingly seen several revered names depart in search of silverware down the years.

Many of those expensive sales did manage to fulfil their trophy ambitions elsewhere, and whether Spurs reinvested the money received well for each of them is firmly up for debate.

Here, Sports Mole looks at the most expensive sales in Tottenham Hotspur's distinguished history.

10. Kieran Trippier - £18.7m

To: Atletico Madrid
Date: July 17, 2019
Age at the time: 28
Tottenham appearances: 114
Tottenham goals: 2

Honours at Tottenham

None

9. Robbie Keane - £20.4m

To: Liverpool
Date: July 28, 2008
Age at the time: 28
Tottenham appearances: 306
Tottenham goals: 122

Honours at Tottenham

8. Christian Eriksen - £23m

To: Inter Milan
Date: January 28, 2020
Age at the time: 27
Tottenham appearances: 305
Tottenham goals: 69

Honours at Tottenham

None

7. Michael Carrick - £23.1m

To: Manchester United
Date: July 31, 2006
Age at the time: 25
Tottenham appearances: 75
Tottenham goals: 2

Honours at Tottenham

None

6. Steven Bergwijn - £26.6m

To: Ajax
Date: July 8, 2022
Age at the time: 24
Tottenham appearances: 83
Tottenham goals: 8

Honours at Tottenham

None

5. Luka Modric - £29.8m

To: Real Madrid
Date: August 27, 2012
Age at the time: 26
Tottenham appearances: 160
Tottenham goals: 17

Honours at Tottenham

None

4. Dimitar Berbatov - £32.3m

To: Manchester United
Date: September 1, 2008
Age at the time: 27
Tottenham appearances: 102
Tottenham goals: 46

Honours at Tottenham

3. Kyle Walker - £44.8m

To: Manchester City
Date: July 14, 2017
Age at the time: 27
Tottenham appearances: 229
Tottenham goals: 4

Honours at Tottenham

None

2. Harry Kane - £80.8m

To: Bayern Munich
Date: August 12, 2023
Age at the time: 30
Tottenham appearances: 435
Tottenham goals: 280

Honours at Tottenham

None

1. Gareth Bale - £85.9m

To: Real Madrid
Date: September 1, 2013
Age at the time: 24
Tottenham appearances: 237
Tottenham goals: 71

Honours at Tottenham