Erik ten Hag broke Sir Alex Ferguson’s transfer rule with Manchester United deadline day move

United were forced to enter the market in the final days as they searched for a short-term fix at left-back. Erik ten Hag had been left with Alvaro Fernandez as his only natural left-back following news of a muscular issue suffered by Luke Shaw.

Tyrell Malacia has also been absent and Ten Hag&aposs need for experience meant he started Diogo Dalot at left-back against Nottingham Forest. The Dutchman had identified a number of loan options to approach in the final week of the transfer window, including Marc Cucurella and Marcos Alonso.

Cucurella was United&aposs first-choice option, but the club refused to meet Chelsea&aposs demands. Instead they made contact with London rivals Tottenham and Reguilon&aposs season-long loan was confirmed on Friday.

It&aposs been 15 years since the two clubs last negotiated over a transfer, with Tottenham&aposs approach to selling Dimitar Berbatov irking Ferguson so much that he and David Gill refused to deal with the club again. United had been in talks to sign the Bulgarian all summer but grew frustrated as Daniel Levy kept moving the goalposts, increasing his demands.

Levy dragged talks out until deadline day, eventually forcing United to pay 30.75million for the striker. Ferguson later opted against bidding for Luka Modric, describing talks with the Spurs chairman as “more painful than my hip replacement”.

“You cant discuss both sides of the issue with Daniel,” the former Reds boss said. “Its about him and Tottenham, nothing more, which is no bad thing from his clubs perspective.”

In the 13 years since, United have held an interest in multiple Tottenham players but seemingly never wanted to push forward. Christian Eriksen revealed that Louis van Gaal, Jose Mourinho and Ole Gunnar Solskjaer all wanted him at Old Trafford, while Mourinho also wanted Eric Dier in 2017.

The approach for Reguilon was likely helped by the fact that he has been deemed surplus to requirements at Tottenham, whereas Berbatov and the other targets were star players at the time.

The transfer window will soon close and although United got their hands on three players well in advance of the September 1 deadline, with Rasmus Hojlund joining Mason Mount and Andre Onana at Old Trafford, activity has stalled since Hojlund&aposs announcement.

A goalkeeper, a midfielder and a striker were Erik ten Hag&aposs priorities heading into the summer window, but injuries early on in the season mean United are in need of further reinforcements.

Our team of experts will be on top of all the goings-on at Old Trafford for the remainder of the window and beyond, and you can get the latest updates and inside information to your phone by joining our new free WhatsApp community below.