It has been a summer of upheaval at Tottenham Hotspur, with a new manager and handful of new players moving to North London.
To balance the books and mould the first-team squad that Thomas Frank wants, a host of fringe men have also left Spurs over recent months.
Tottenham have signed Xavi Simons to add creativity to their attacking options, in what may be the last signing for the Premier League club before the transfer window closes on Monday evening.
But there are a host of players surplus to requirements that could well leave in the next 48 hours.
For one former Tottenham player however, despite leaving N17 in May, he has still not found a new club.
The demise of Sergio Reguilon
Tottenham announced in May that a number of players had left the club after the culmination of their contracts.
This included Spanish defender Sergio Reguilon, who ended a five-year affiliation with the North London club.
Tottenham spent £28 million to sign the left-back from Real Madrid in 2020, with the deal seen as quite the coup at the time.
Despite Reguilon representing Spain at senior level, the defender has failed to perform consistently in England.
With the full-back a free agent and able to join a new club for free, the fact he has not been able to secure a move to his next team after almost three months speaks volumes.
Wasted transfer funds by Spurs
Reguilon was farmed out to both Brentford and Manchester United on loan during his time in England, but was not able to impress enough to secure a permanent transfer to either.
The Spanish defender joins a long list of players that Tottenham have spent significant funds on, only for them to fail to deliver in the Premier League.
Reguilon clearly has quality – you don’t play for Spain and Real Madrid without having a pedigree at the highest level.
However, the 28-year-old needs a fresh challenge to reignite his career – most likely back in Spain – but is yet to find an employer willing to take a chance on him.