Tottenham Hotspur haven’t exactly been the biggest spenders throughout the history of English football, but that does not mean that they’re without their expensive arrivals. Last summer, in particular, Daniel Levy has decided to splash the cash on funding the Antonio Conte era. The Italian seems to have a clear plan - a plan that Levy clearly believes in - as he looks to end Spurs’ wait for silverware.
So far this summer, the North London club have welcomed five new arrivals, with Richarlison the most expensive of the lot. Considering the money that they’ve spent, the pressure will be on, but, if anyone can handle that pressure, it is serial winner Conte.
Last season, the Italian, particularly in the second-half of the season, seemed to transform Spurs into one of the most difficult sides to beat in the league, with even Liverpool failing to beat them at Anfield of all places.
With that said, we took a deeper dive into Spurs’ transfer history to find out their 20 most expensive signings of all time, via TransferMarkt.
20) David Bentley - £19.8 million
Bentley arrived at Spurs with a big reputation but it barely worked out for him.
Having come through the ranks at Arsenal, he did score a world-class goal in the north London derby, swiveling on the ball around 40 yards from goal before volleying it home.
That was as good as it got, though, as he only played 62 times for the club. Perhaps his most iconic moment was pouring water over Harry Redknapp after Spurs qualified for the Champions League.
19) Luka Modric - £20.25 million
An absolute steal.
Modric is perhaps one of the best signings on this list and for good reason.
Modric arrived from Dinamo Zagreb and went on to pull the strings at Spurs for a number of years, and then earned a major move to Real Madrid.
Since then, he's won almost everything, even inspiring Croatia to the World Cup final. What a player.
18) Darren Bent - £22.28 million
Bent's spell at Tottenham can be summed up by the fact that he missed a major chance at the back post at White Hart Lane, and Harry Redknapp subsequently said that he felt his wife could have scored it.
Bent arrived from Charlton Athletic as a prolific goalscorer, but he could only score 25 times for the club.
That return just isn't good enough, and the cash splashed was far from worth it.
17) Serge Aurier - £22.5 million
Aurier came in to solve the right-back issue and did not really manage to do that.
Having sold Kyle Walker, and also seen Kieran Trippier's form decline, Spurs looked to the PSG man to add some dynamism down the right flank and into defence.
He was famously rash, though, and repeatedly struggled with the defensive side of the game.
Aurier is now at Nottingham Forest.
16) Emerson Royal - £22.5 million
Emerson remains in the Spurs squad and is continuing to play under manager Antonio Conte.
However, the jury is out as to whether he's been anything close to a success.
While he is defensively solid, he's very poor going forward - the exact opposite of Aurier - and Spurs made a move to sign Pedro Porro as his replacement in January.
15) Bryan Gil - £22.5 million
Gil has already been loaned back to Sevilla.
The young Spanish winger did show flashes of his talent earlier this season, as he came into the fold amid a poor run of form for the club.
However, he has not been given the chance to continue that development in north London and has been sent back to Spain, from whence he came.
The jury is firmly out.
14) Ryan Sessegnon - £24.3 million
Sessegnon plays regular football for Spurs but it's questionable as to whether he's been anything close to a success.
He has made 56 appearances for the club in total, scoring three goals and only registering four assists.
For an attacking left-back, that really isn't an inspiring return, especially given the money spent on him.
Again, the jury is out.
13) Lucas Moura - £25.56 million
This one has to go down as a hit.
Lucas may have reverted to a backup squad player this season but he is forever a Spurs legend for that hat-trick against Ajax in Amsterdam in the Champions League semi-final second leg.
Without the little Brazilian, Spurs would never have reached that Champions League final, and he'd be worth the money for that alone.
In total, he has scored 38 goals and registered 27 assists in 213 games. Not bad at all.
12) Yves Bissouma - £26.28 million
Bissouma has yet to really prove himself at Spurs and injury issues have reared their ugly head.
Snapped up from Brighton, the midfielder has only played 25 times for the club, and is now out for up to eight weeks, as he needs surgery on his ankle, as per The Daily Mail.
It's really not possible to judge him, as a result, but he will be desperate to get back into the team after completing his recovery.
11) Heung-min Son - £27 million
The biggest success on this list, without doubt.
Son was snapped up from Bayer Leverkusen way back in the 2015/16 season and has gone on to become an absolute hero at Tottenham.
Having forged an almost telepathic understanding with Harry Kane, Son has scored 139 goals and laid on 77 assists in 355 games.
That's an incredible return given the investment.
10) Erik Lamela - £27 million
Lamela became a cult hero at Spurs.
Having been signed in the wake of Gareth Bale's exit to Real Madrid, the Argentina international was meant to be the direct replacement.
That didn't quite work out as he couldn't replicate Bale's unbelievable exploits, although he did score 37 goals and lay on a further 47 in 257 games.
He was sold to Sevilla last summer, with cash and Bryan Gil coming the other way.
9) Sergio Reguilon - £27 million
Reguilon looked like a nailed-on hit.
Signed from Real Madrid, the left-back looked to be coming into the club to fix the defensive woes down the left side, following Danny Rose's alarming dip in form.
However, Reguilon made just 67 appearances for the club and is now playing for Atletico Madrid on loan.
A flop, unfortunately.
8) Roberto Soldado - £27 million
Oh dear.
Soldado came into Spurs with a huge reputation.
He was going to be the man to take them to the next level, scoring goals left, right and centre, and elevating them into contenders.
Soldado actually scored just 16 goals in 76 games for the club, and was eventually moved on, joining Villarreal in his native Spain.
7) Steven Bergwijn - £27 million
Another flop. Maybe Spurs just aren't very good at these transfers.
Bergwijn arrived in the January transfer window under the management of Jose Mourinho and while he electrified the stadium with a stunning debut against Manchester City, as he scored a superb volley, he only had fleeting moments thereafter.
Bergwijn also scored two injury-time goals to beat Leicester City in one of the most dramatic games of last season, but he simply wasn't allowed to stake a regular claim.
He's now playing back in the Netherlands.
6) Giovani Lo Celso - £28.8 million
What more can be said about Lo Celso?
The Argentine came in and it looked as though he was going to be the spiritual successor to Christian Eriksen in the Spurs midfield.
Instead, he had just 14 goal involvements in 84 games, and is now on loan at Villarreal.
It's fair to chalk this one up as a flop.
5) Moussa Sissoko - £31.5 million
Sissoko may have been a figure of fun but under Mauricio Pochettino, he became a vital cog in the team that reached the Champions League final.
He was developed into a box-to-box midfielder, with his lung-busting energy proving vital to dictating the tempo.
Sissoko may have been slightly limited in what he could do, but he proved an important player.
It's hard to say this one wasn't a hit, ultimately.
4) Davinson Sanchez - £37.8 million
Sanchez arrived to become the new fulcrum of the Spurs defence but it's not really worked.
Sanchez is hugely limited, with his ability on the ball seeing him dropped from the first-team by Antonio Conte.
If everyone is fit, the Colombia international won't play for the club, and for a signing worth just under £40m, that absolutely isn't good enough.
3) Cristian Romero - £44.3m
Already a World Cup winner, having lifted the trophy with Argentina, Romero looks a sensational signing.
He's an excellent defender, although he can be a little bit too aggressive, as evidenced by his sending off against Manchester City.
It's worth noting that, without him, Spurs then lost 4-1 to Leicester and looked all at sea defensively.
That's no coincidence.
2) Richarlison - £52.2 million
Spurs splashed the cash to bring the attacker in from Everton but he's yet to really be given a fair shake at the club.
The Brazil international, who sparkled at the 2022 World Cup, has made just nine starts for the club this season.
He has scored twice in the Champions League, though, and looks primed to take every game by the scruff of the neck when he is on the pitch.
More opportunities are surely coming.
1) Tanguy Ndombele - £54 million
Ndombele remains Spurs' club-record signing, which is a major indictment of the club's recruitment strategy.
Ndombele played 91 times for the club but could only register 19 goal involvements and has already seemingly been consigned to the flop list.
He is now on loan at Italian club Napoli, and it seems inevitable he'll be moving on in the summer.
We can't see Spurs making a profit, here.