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Later that same month, Reguilon moved to Tottenham Hotspur on a permanent deal. Managed by former United boss Jose Mourinho, Sergio made his debut for the club on 29 September 2020 in a Carabao Cup win over Chelsea.
His Premier League bow would soon follow, in a 6-1 win at Old Trafford on 4 October, and he scored his first Spurs goal on 21 November in a 2-1 triumph over Leeds. Sergio made 36 appearances in all competitions during his first season with the North London club, assisting six goals. He played 31 times in the following campaign before he missed the latter part of it due to a groin problem.
Reguilon returned to Spain by joining Atletico Madrid on loan for 2022/23, but injury limited him to 12 appearances and he was back at Spurs in the summer of 2023.
On 1 September 2023, Reguilon arrived at United on loan from Spurs, becoming our fifth addition of the summer transfer window and the seventh Spaniard to sign for the club.
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