With yet another big money move failing miserably, as Tanguy Ndombele saw his contract ripped up, we've taken a look at five of the WORST signings the club have made since 2010.
From the likes of Ndombele, Moussa Sissoko, and Giovani Lo Celso who all joined the club in expensive deals, not everyone could be included, but here are our top five picks.
In at first, and it's no surprise at all, is club record signing Tanguy Ndombele, who joined Tottenham Hotspur from Olympique Lyonnais in July 2019 for a £63m fee.
Having been the heartbeat of a strong Lyon side in the previous campaign, there was plenty of excitement from Spurs fans as it seemed they were completing a deal for one of the most promising talents in world football.
The Frenchman signed a six year contract at the club, however, one year before his deal was due to expire, Tottenham announced they would be terminating his contract, bringing an end to a disappointing five year spell in North London.
Struggling to find rhythm at the beginning of his time in N17, he was lambasted by Jose Mourinho in March 2020, with the Portuguese manager opting to hook Ndombele off at half time after the midfielder failed to make a single sprint in a 1-1 draw at Turf Moor.
The 27-year old did manage to make a heroic turnaround to his career in Lilywhite, having a splendid second season. He registered six goals and made four assists in all competitions, however Mourinho's dismissal towards the end of the season ruined the momentum he had gained.
Out of favour under Ryan Mason and Antonio Conte, despite a mediocre spell in the team under Nuno Espírito Santo sandwiched in the middle, Tanguy Ndombele would play his last ever game for Tottenham in January 2022.
With 69 minutes on the clock and the side trailing at home to Morecambe in the FA Cup, Ndombele was booed by fans as he trudged across the entire with of the pitch, bringing a close to his time at the club.
Loan terms at Lyon, Napoli and Galatasaray never enabled the midfielder to rekindle the form from his early days, and he has now been released by Spurs, costing them £5m.
After scoring thirty goals across all competitions with Valencia in the 2012/13 season, Roberto Soldado joined Tottenham in a club record £26m deal in August 2013.
With Gareth Bale moving to Real Madrid, the Spanish striker was brought in, alongside a number of other signings, to combat the huge void left by the Welsh Wizard.
However, after two years in North London, he was sold back to La Liga for a fraction of the fee originally paid by Daniel Levy.
Soldado's start to life in North London was surprisingly good considering how the rest of time at Tottenham panned out. He scored four goals in his first three appearances in a Lilywhite shirt, but after this, he only went on to net on twelve more occasions in 73 appearances, leading to him being sold after a massively underwhelming time at the club.
It was a Monday night in April which sparked the beginning of the end for the striker. Twenty year old Harry Kane was given the nod by Tim Sherwood to start in Soldado's place, and he never looked back.
The former Real Madrid and Getafe attacker had been displaced by the new kid on the block, and that continued under the leadership of Mauricio Pochettino, forcing the Spaniard to look for pastures new.
He would go on to score a sole goal in the 24 games he would play in the Premier League 2014/15, before leaving for just £7m.
What could've been. *sighs*
Despite not being signed for a hefty fee, the expectation versus reality when it came to the signing of Clinton Njie in 2015 was a rude awakening to both Tottenham fans and the club hierarchy.
The Cameroonian attacker missed a staggering 28 matches with a knee injury in his first and only campaign in North London, where he featured just fourteen times. He registered a sole assist for Mauricio Pochettino's side, who finished third and narrowly missed out on the title.
The following season, he was loaned back to France, joining Olympique Marseille and he made that move a permanent one in 2017 for a fee around £5m.
Due to the fact he hardly featured at White Hart Lane, playing just 386 minutes across all competitions, there really is not much more to add about Clinton Njie - who his now plying his trade in Turkey with Sivasspor.
Another victim of the "Magnificent Seven" who joined during that infamous summer 2013 transfer window - this time it's Paulinho. The midfielder joined from Brazilian giants Corinthians for a fee of around £17m - a club record at the time.
Drawing comparisons to Frank Lampard due to his goalscoring capabilities from midfield, the signing sparked plenty of hope amongst the Tottenham fanbase that they were about to sign a future great. Little did they know, things would soon turn sour and the Brazilian would leave for the Chinese Super League just two years later.
Prior to arriving in North London, the 35-year old had netted 34 goals in 167 appearances for Corinthians, as well as beating Chelsea in the Club World Cup final and Spain in the Confederations Cup final.
With 17 caps to his name for five time World Cup winners, Brazil, Spurs fans believed they were signing a star.
Despite being directly involved in seventeen goals (10G, 7A), in his time in the capital, Paulinho was a complete shadow of the package fans were expecting.
He fell down the pecking order under Mauricio Pochettino and even stated: "I did not want to leave my apartment in London because I was so stressed about not playing," in an interview with the Players' Tribune.
Considering the potential he had, it's a shame that all the Brazilian will be remembered for is his last minute back-heel winner away at Cardiff City, and being sent off for kicking Luis Suarez in the shoulder in a 0-5 loss against Liverpool at White Hart Lane.
A surprise inclusion that will stun many, but it's safe to say that cult hero Moussa Sissoko was nowhere near good enough to warrant being signed for a club record £30m fee.
There is no denying that he did actually manage a couple of good years in his time in North London, most notably during the final year with Mauricio Pochettino and under Jose Mourinho, but overall, his time at the club was rather unconvincing.
After Tottenham opted against signing Sadio Mane in order to stay in line with their tight wage structure, Daniel Levy ended up pulling the trigger on a panic buy on deadline day in summer 2016, with Moussa Sissoko swapping the North East for North London.
The Frenchman, who was primarily used as a right winger at Newcastle United, came under heavy criticism at the culmination of his first campaign with the Lilywhites, where he had played the full ninety minutes on just four occasions, and his second season in the famous white strip wasn't much better.
Pochettino's final full campaign in N17 was horrifying, however Sissoko was actually one of few bright sparks aside from the memorable UEFA Champions League run.
He would go onto continue that rich vein of form under Jose Mourinho and was one of the first names on the team sheet, however, as soon as the legendary coach left, Sissoko was straight out of the team, featuring for just ONE entire minute in the league under Ryan Mason, who had six games in charge.
Sissoko never set the world alight, nor was he appalling, but with the fee being taken into consideration and the fact that he offered very little in return, means he is harshly included in this list.