Manchester United’s signing of Sergio Reguilon is the first time they have dealt directly with Tottenham since signing Dimitar Berbatov in 2008.
The left-back is joining United on a season-long loan deal in an agreement that includes a break clause in the January transfer window. The Red Devils are not paying Spurs a transfer fee for the deal, but they will cover the player’s wages.
Reguilon has made 67 first-team appearances for Spurs but had not been involved in their first-team plans, spending the second half of last season on loan at Atletico Madrid. He is hopeful of being involved in United’s matchday squad for Sunday’s trip to Arsenal.
Erik ten Hag had been on the lookout for a new left-back due to injuries to Luke Shaw and Tyrell Malacia, while Brandon Williams has left Old Trafford to join Ipswich on a season-long loan deal. Diogo Dalot, primarily a right-back, deputised in the position in Saturday’s home win over Nottingham Forest.
United had not dealt with Spurs since signing Berbatov in the summer of 2008, having signed Michael Carrick from the club two years prior. However, the nature of Spurs' negotiating strategy over Berbatov irritated senior United figures.
Marcel Sabitzer completes Man Utd transfer after last-minute deadline day dashSir Alex Ferguson and former CEO David Gill vowed they would never deal with the north London club again due to the nature of the negotiations, and for the remaining five years of their tenures they did not return to Spurs for any players.
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While 15 years have passed since that Berbatov deal, the impasse between the clubs has remained – until now. Just like the signing of the Bulgarian striker in 2008, the move for Reguilon comes on the final day of the summer transfer window.
It is unusual for two clubs of their stature in the same league not to conduct any business between each other whatsoever, but that has been the case between Spurs and United. By contrast, United have signed players from Chelsea in recent years including Mason Mount, Nemanja Matic and Juan Mata.
Ironically, United's move for Reguilon only came after ruling out signing their preferred target - Marc Cucurella of Chelsea - broke down. His appearance for the Blues in their EFL Cup win over Wimbledon this week ensured he would not be able to go out on loan separately later in the season were United to end the deal at January's break clause.
Reguilon is United’s fifth signing of the summer transfer window following the arrivals of Mount, Andre Onana, Rasmus Hojlund and Altay Bayindir. The Red Devils are hopeful of finalising their summer transfer window with the arrival of midfielder Sofyan Amrabat from Fiorentina.