Rewind five years, Tottenham Hotspur had just smashed their transfer record to bring in Tanguy Ndombele from Olympique Lyonnais, in what was the club's first signing in eighteen months.
Mauricio Pochettino, with the help of Lucas Moura, had miraculously dragged his men to a UEFA Champions League final in the previous campaign and was now being backed by the board with funds to improve his playing squad, having not made a single signing in the previous two transfer windows.
Spurs remain the only club in Premier League history to go a whole summer window without adding one player to their ranks, yet somehow that no-show in 2018 ranks nowhere near the horror show which is the 2019 summer transfer window.
Money spent, but not wisely
Daniel Levy allowed Pochettino to splash the cash on his top targets, with the Lilywhites spending £200m on Tanguy Ndombele, Jack Clarke, Giovani Lo Celso and Ryan Sessegnon.
Five years later, not one of these four remain at the club, and they all left for a combined fee of just under £10m. Spurs opted to release Ndombele, but that alone set them back a measly £5m to do so. In total, they have had to settle for a £190m loss and that is before we include the large sum that the quartet ate up in wages.
Tricky French midfielder Ndombele was not the only one to be sold for nothing, with Spurs refusing to take up the one-year extension clause in Ryan Sessegnon's contract, meaning he was released for free.
Giovani Lo Celso was sold for just £8.4m, with the only saving grace being the £5m Spurs recuperated from the sell-on clause included in Jack Clarke's £750k move to Sunderland.
Arguably the most disappointing thing about this summer spending spree was the fact that each of the four players showed glimpses of quality throughout their time in N17, and before they made the big-money switches to the Premier League.
Injury struggles overshadow Spurs careers
There is no denying that each of the formidable four had quality, but three of them suffered horrific injury problems during their spells with Tottenham.
The trio of Ndombele, Lo Celso and Sessegnon never got going in a Spurs shirt, with lengthy and repetitive injuries causing them plenty of grief throughout their five years in North London. Overall, the former Fulham man has missed a whopping 798 days since he signed his deal with Spurs in the summer of 2019, sitting out of a staggering 127 matches.
His counterparts weren't let off lightly either - Argentinian midfielder Lo Celso suffered slightly less than the Englishman, with Ndombele being let off but still facing a torrid time on the sidelines, with eight separate injuries in his first two years at the club. Combined, the midfield duo missed 84 games throughout their Tottenham career.
Where are they now?
Tanguy Ndombele
New club: OGC Nice
Having been released from his contract at the Tottenham Hotspur Stadium, Ndombele returned to his home country, putting pen to paper on a two-year deal with OGC Nice.
When the deal was announced, Club President Jean-Pierre Rivère stated that "over the course of our meetings, I encountered a charming and motivated young man," so it will certainly be interesting to see whether the Frenchman can return to his very best at the INEOS-backed side.
Jack Clarke
New club: Ipswich Town
Jack Clarke made the switch to Sunderland in the North East when he left The Lilywhites in 2022, but he now finds himself in Suffolk at The Tractor Boys, and in the Premier League where the player has shown he belongs.
He scored 28 times and assisted on 22 occasions during his two-and-a-half seasons in the EFL with The Black Cats, helping them earn promotion back to the Championship. His starring role in their side him earn a move to Ipswich for £15m, plus £20m in add-ons, meaning Tottenham secured £5m from the 25% sell-on clause they inserted into the deal when Clarke left North London.
Giovani Lo Celso
New club: Real Betis
Five years on from swapping Los Verdiblancos for the Premier League, the Argentinian midfielder has returned to his former club for just a fraction of the £42m that Tottenham originally paid for him.
It never worked out for Lo Celso in the capital, and he was shipped out on loan to Villarreal for eighteen months, before finally rekindling some of his best form under Ange Postecoglou. Unfortunately for the two-time Copa America winner, broken promises saw him wanting to leave, and he was granted his wish on deadline day.
Ryan Sessegnon
New club: Fulham
Another player who joined in 2019 and has now completed a full circle is Ryan Sessegnon, who rejoined boyhood club Fulham on a free transfer after a five-year stint at Tottenham Hotspur.
The versatile left-sided player saw his Spurs career plagued by injuries, and fans never got to see the potential he showed during the early years of his Tottenham career at The Cottagers.
A disastrous spending spree that signalled a change in tack from Levy
Judging by the disgust from some Spurs fans, and their blame on Daniel Levy and his "inability" to spend large sums of money, you would expect Spurs have spent very little since their first big window in 2019, but this is far from the truth.
Many have passed the blame to the transfer window in the summer of 2019 when Spurs spent £200m, believing that due to the failure of those summer signings, the chairman now refuses to cough up hefty transfer fees and instead opts for the "cheaper option."
Five years on from announcing the record signing of Tanguy Ndombele, Tottenham broke the stat by completing a £65m deal to sign Dominic Solanke. They have also made the £50m purchase of Brennan Johnson and lumped big fees on Pedro Porro, Cristian Romero and Micky van de Ven (all upwards of £40m).
While some critics still level complaints over Levy's spending, the facts paint a story of consistent spending over the last five years. Since the Champions League final defeat in Madrid, Spurs have spent €645.2m before add-ons were included.
Although some may question the quality of the players purchased, there is no doubt that Levy's now lack of involvement with the football side of transfers, with director Johan Lange and Rob McKenzie now leading the recruitment of players, has led to the creation of a very exciting era on the white side of North London.
Finally, they are competing with their noisy neighbours and it is a matter of time before success finally returns to the club after 16 long years.