Now, just three years later, Reguilon has arrived at Old Trafford as United look to plug holes in their squad created by injuries.
Tottenham were happy to let Reguilon leave but may live to regret letting him leave quite so easily to a potential top-four competitor.
Despite being at the club for three years, Reguilon was quick to fall out of favour at Tottenham. A string of poor performances at the end of the 2020/21 season and a lack of cutting edge under the ruthless Antonio Conte saw Reguilon become something of an outcast at Spurs.
A loan to Atletico Madrid followed, however, Reguilon played just 11 league games for Diego Simeones side. This is not to say Reguilon could not be improved defensively by Erik ten Hag.
So, is a player who has not played consistent football for nearly two seasons a strong candidate to be a starter for United, at least until one of Shaw and Malacia are fit again?
Reguilon was dropped by Conte due to his lack of cutting-edge in front of goal. Conte has always demanded that his wing-backs are attack-focused and strong in front of goal.
At United, Reguilon will not be asked to be a ruthless finisher and will have much less attacking onus placed on him, even if Ten Hag does like his full-backs to push forward. In his last playing season at Spurs, the 26-year-old scored two goals and chipped in with three assists across 25 games.
Reguilon was a strong crosser during his time at Spurs under Mourinho and Nuno Espirito Santo. His crossing ability will be appreciated by Ten Hag at United and could be a huge asset with a target like Rasmus Hojlund to aim for in the middle. United have plenty of options out wide, but you&aposd struggle to pick out a player who will consistently deliver for Hojlund to score the goals that will help him be labelled a success – Reguilon may be his man.
Defensively, Reguilon struggled towards the latter end of the 2020/21 season, but a lot of time has passed since then and a loan under Simeone can&apost have done him any harm.
It is perhaps easy to forget how young Uniteds new left-back was when he moved to England, and just how young he still is. At 26, he is two years younger than first-choice left-back Shaw and just two years Malacias senior.
While the new United loanee has been without regular football for quite some time now, he has got a lot to prove, with Spain manager Luis de la Fuente no doubt watching on ahead of next year&aposs European Championship.
The Spanish full-back is no longer the 23-year-old who signed for Tottenham full of promise. At 26, he is entering the prime years of his career and United will be hoping the three years of experience he has gained since they missed out on Reguilon in 2020 will help them while they deal with the injuries.
