Manchester United's deadline day loan of Sergio Reguilon is the first time they have dealt directly with Tottenham since 2008 after former boss Sir Alex Ferguson encountered issues with the north London side.
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's 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.
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