Tottenham were presented with an opportunity they simply couldn't turn down in September 2020. Adding to the squad in Jose Mourinho's first summer as head coach, a new left-back wasn't a priority for the club ahead of the 2020/21 campaign with Ben Davies and Ryan Sessegnon already on the books.
However, the chance to sign Sergio Reguilon was one they couldn't pass up after a standout campaign on loan at Sevilla. Previously getting so much joy from Kyle Walker and Danny Rose in the full-back positions, Tottenham's position of strength had quickly diminished with the former moving on and the latter struggling to recapture his best form after a serious injury.
Registering three goals and five assists in his time with Sevilla, it appeared that Tottenham had solved their issue at left-back with the attack-minded Spaniard joining from Real Madrid. The early signs were extremely positive, with the 25-year-old impressing going forward and quickly registering brilliant assists in the wins over West Ham and Brighton & Hove Albion.
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Almost two years after his move to Tottenham Hotspur Stadium, Reguilon's time in north London is ending as he is no longer in Antonio Conte's plans and surplus to requirements. So where exactly did it go wrong for the Spain international?
Quite simply, Reguilon has failed to make the transition to Conte's Tottenham system. Immediately opting for a 3-4-3 formation following his appointment as boss, the setup seemed ideal for the left-back due to his attacking qualities. There is a notable difference between playing as a left-back and a left-wing-back, though, and it is something the Spaniard, who has played as a left-back his whole career, has had problems with.
Unable to replicate the form he displayed in his first few months at Tottenham last season in the capital, Reguilon's assists dropped from six to three, but he did contribute with two goals. Eventually losing his place in the side to Sessegnon, who is a natural in the role, the writing was on the wall for the player once Ivan Perisic joined on a free transfer from Inter Milan.
One of four players left out of Spurs' South Korea pre-season tour plans and then absent for the Rangers and Roma friendlies, Conte made it clear in Israel that the quartet had been informed about the plans for the season and that they deserve to play games regularly. Moving on Giovani Lo Celso and Tanguy Ndombele to Villarreal and Napoli on loan move over the past week, Reguilon and Harry Winks still remain at the club ahead of deadline day.
Tottenham have eleven days remaining to conclude their transfer business, and in that time, they will be hoping to agree on moves for both players. Both regulars in the Spurs side in recent years, the duo certainly shouldn't be short on suitors as they do have qualities that would benefit a number of clubs.
While, of course, some moves do tend to drag on until deadline day to come to fruition, many would have predicted that Reguilon would actually be the first of the quartet to move on. He did catch the eye in his first campaign at the club, whereas Lo Celso and Ndombele just couldn't find their top form on a consistent basis in their three seasons at Tottenham.
Although his form may have dipped in his second season at the club, it is perhaps strange to still find Reguilon at Tottenham Hotspur Stadium with deadline day edging ever closer. Linked with some big clubs in Spain and Italy, Sevilla were tipped to re-sign him, but that kind of went out of the window once they had signed left-back Alex Telles from Manchester United on loan.
According to The Athletic, Nottingham Forest, Tottenham's opponents, on Sunday afternoon, are keen on the player and talks are believed to have taken place over the past couple of weeks regarding a loan deal. Quite whether he heads to the City Ground or elsewhere before 11pm on Thursday, September 1, remains to be seen.
Excelling for Tottenham in his first season at the club, nobody could have predicted Reguilon's current predicament one year ago, let alone two years ago. After all, Real Madrid were seen as his most likely destination if he was to depart Tottenham due to their buy-back clause option in the summers of 2021 and 2022.
Both Spurs and the player will now be hoping for a quick resolution, though, with time quickly running out in the summer transfer window. Reguilon certainly needs that to be the case to get his career back on track after a summer to forget at Tottenham.
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