In the summer of 2023, Tottenham Hotspur finally said goodbye to record goalscorer Harry Kane, who left for Bayern Munich after months of speculation. The bid, worth an initial €100m (£86.4m) according to the BBC, is one of the biggest sales in Premier League history.
But where does it rank for Tottenham themselves? We have taken a look at who Spurs have received the big bucks for over the years.
Rank
Player
Sold to
Fee
Harry Kane
Bayern Munich
Gareth Bale
Real Madrid
Kyle Walker
Man City
Dimitar Berbatov
Man Utd
Luka Modric
Real Madrid
Steven Bergwijn
Ajax
Oliver Skipp
Leicester
Kieran Trippier
Atletico Madrid
Robbie Keane
Liverpool
Michael Carrick
Man Utd
10 Michael Carrick to Manchester United – £18.6m
This was quite a bit of money back in 2006, but Spurs will almost certainly look back on this with regret. Michael Carrick would go on to be a fixture with United, playing 11 full seasons there and winning absolutely everything.
But perhaps this was the start of an unfortunate trend for Spurs. Here they were with a world-class talent, only to sell him on to another club where he’d be much more successful.
There was little suggestion that Carrick would stay at Tottenham, but it’s a trend they’ve yet to really pull out of.
The £18.6m fee they received just wasn’t worth losing Carrick in the end – and it wouldn’t be for the last time we say that.
9 Robbie Keane to Liverpool – £19m
Here’s a bizarre one. Robbie Keane was Spurs’ star player in 2008, and Liverpool signing him for £19m was a real statement of intent from the Reds – and a serious blow to Tottenham.
He was their captain, after all, and Daniel Levy publicly spoke of their disappointment that Keane wanted a move. But not to worry! He was back within six months.
Liverpool signed Keane on the idea that he’d form a tandem with Fernando Torres, allowing Steven Gerrard to shift back into midfield.
Only, it quickly became apparent that Torres and Keane were nowhere near as good a partnership as Torres and Gerrard were, with the Irishman finding himself on the bench.
The Reds wanted to sell, and Spurs were all too happy to get him back, initially on loan, in the next transfer window.
8 Kieran Trippier to Atletico Madrid – £20m
Kieran Trippier was a very well-regarded right-back at Spurs, but never actually played more than 27 Premier League games in a season. It wasn’t an enormous shock that he moved on to Atletico, then – but again, in hindsight, he’s a player Tottenham would rather have kept.
Trippier enjoyed a fantastic two and a half years in Madrid, even winning La Liga in 2021. He’d bring it to an end in 2022, though, as one of the headline signings of Newcastle United’s new era.
He’s since become one of the best right-backs in the Premier League, winning the Magpies’ Player of the Year award in 2023 as they finished 4th. So again, the £20m that Spurs received doesn’t quite look worth it.
7 Oliver Skipp to Leicester – £25m
After failing to muscle his way into Ange Postecoglou’s first-team plans, Oliver Skipp called time on his stay at Spurs to join newly promoted Leicester City in the summer of 2024.
Skipp also struggled for game time in his first campaign at the King Power, so Tottenham collecting £25m for his services certainly looks a great deal from their point of view.
6 Steven Bergwijn to Ajax – £26m
Tottenham signed Steven Bergwijn in January 2020 and were hoping he’d further boost a very exciting attacking lineup at the club. Here was a player who could back up Son Heung-min, essentially.
It just never really worked out. Bergwijn rarely started and just wasn’t the attacking threat Spurs had hoped for. Scoring just eight goals in 83 appearances wasn’t exactly worth what they paid for him.
Fortunately, Ajax were happy to take him back to the Eredivisie and paid £26.4m for the privilege – essentially what Spurs paid PSV Eindhoven in the first place.
5 Luka Modric to Real Madrid – £30m
This one possibly hurts the most – until Kane’s departure, perhaps. Luka Modric was an outstanding player for Tottenham, running their midfield and becoming one of the most talented midfielders in the Premier League.
His move to Real Madrid, costing around £30m, didn’t go well at first – he was named the worst transfer in La Liga during his first season.
But to say things turned around is an understatement. Modric has since gone on to become one of the greatest and most successful midfielders of all time. That’s really not overselling it.
Spurs sold him for £30m plus ‘an agreement’ with Real that had president Florentino Perez “[looking] forward to working closely with Tottenham in the coming years”. We’ll get to that one soon enough…
But as for Modric, Spurs didn’t have too much choice as he did want to leave the club. Still, to have such a talent on your books and come away with little to show for it – that hurts.
4 Dimitar Berbatov to Man Utd – £30.75m
Dimitar Berbatov – a great player who was the absolute antithesis of the modern-day footballer. He wasn’t quick, he didn’t run about or press, there wasn’t much hard work involved, and he rarely showed any emotion on the pitch. Like the anti-Wayne Rooney.
United, though, saw him as the right player to add to Rooney, Carlos Tevez and Cristiano Ronaldo – and would be proven right. Berbatov not only scored goals for Spurs, after all, but was a perfect link-up player and one of the most technically sound players on the planet.
Tottenham really didn’t want to lose him, but after Manchester City also bid at the summer 2008 deadline, they gave in and he joined United for £30.75m – despite having no time to replace him.
Berbatov would, like many others on this list, go on to win the title at his new club and enjoy plenty of success. Same old story, then.
3 Kyle Walker to Man City – £50m
A massive leap in fees here (but get ready for another one) as Spurs made sure City paid exactly what they wanted for Kyle Walker. Honestly, there’s a solid argument that this sale is the best on the list.
Walker has gone on to much success at City, as you’d expect. But with Kieran Trippier already at the club, Spurs got an enormous fee for a player they didn’t even need to properly replace.
It’s just a shame the money wasn’t spent better. Serge Aurier arrived to provide competition for Trippier, while Fernando Llorente was the major signing up top. Juan Foyth arrived, too, with the three of them all coming in for under Walker’s price – but none of them really worked out.
Still, there’s no denying that Spurs got value for Walker, who remains one of the most expensive full-backs of all time at £50m.
2 Gareth Bale to Real Madrid – £85.3m
Remember when Florentino Perez said that he was looking forward to more business with Spurs after the Luka Modric deal? Yeah, that mainly meant he was looking forward to signing Gareth Bale the next year.
This was, at the time, the most expensive move in history as Real paid even more for Bale than they had for Cristiano Ronaldo in 2009. His €100m (£85.3m) transfer was quite shocking to see in 2013.
For those who didn’t witness it, it’s hard to explain just how incredible Bale was at Spurs. He could seemingly do anything, winning the PFA Player of the Year awards in 2011 and 2013.
Some of his goals were just ridiculous – he’d will the ball in from 25 yards while surrounded by players. Many felt he was going to follow in Ronaldo’s footsteps.
Of course, it didn’t quite work out that way at Real. Bale won absolutely everything there and provided some unreal moments with Los Blancos, but never quite reached that best-in-the-world level before petering out in his final years.
Spurs fans, however, will always believe he could have been everything he promised if he’d stayed. Remarkably few – possibly zero – will look back on this sale, even with a world-record fee, without regret.
1 Harry Kane to Bayern Munich – £86.4m
A summer of rumours surrounding Harry Kane’s future became par for the course during his latter seasons at Tottenham, such was the striker’s quality and the club’s perennial inability to match his talent with the silverware it deserved.
Having staved off major interest from Manchester City two years prior, Kane finally departed Hotspur Way after an eighth-place finish left the club trophyless for a 15th straight campaign and out of Europe for the first time since the 2009/10 season.
Bundesliga juggernauts Bayern Munich would be the fortunate recipient of the England captain, who, after rather typically surrendering the Bundesliga title in 2023/24, did go on to win the German top-flight in 2024/25. That was Kane’s first-ever major trophy. Better late than never, eh?
The fee to sell was by no means a paltry one. Spurs got a fair whack for his services, receiving £86.4m, with only the exchange rate placing this one above Bale’s departure to Real Madrid – though add-ons could increase this sale even further.
It will take some doing for any player to hit the heights of Kane and Bale if they are to threaten their places in this list over the coming years.
