Reguilón is a graduate of Real Madrid's youth academy. He made his senior debut in August 2015, while on loan at Logroñés. Reguilón made his first-team debut for Real Madrid in October 2018. He spent the 2019–20 season on loan at Sevilla, where he won the UEFA Europa League and was named in the Squad of the Season. Reguilón signed for Tottenham Hotspur in September 2020.
Reguilón made his senior debut on 23 August 2015, playing the last seven minutes in a 3–0 home win against Compostela. The following 16 January, after being sparingly used, he returned to Los Blancos and was assigned to the reserves also in the third division.[8]
On 23 August 2016, Reguilón returned to Logroñés also in a one-year loan deal.[9] Now an undisputed starter, he scored eight goals during the campaign; highlights included four past Bilbao Athletic on 2 October 2016 (5–3 home win).[10]
Upon returning to Castilla, Reguilón was a first-choice in Santiago Solari's side, and renewed his contract on 11 May 2018.[11] On 25 August of that year, he was promoted to the main squad by manager Julen Lopetegui.[12]
On 5 July 2019, Reguilón was loaned to Sevilla for the 2019–20 season.[15][16] On his official debut on 18 August, he scored the opener in a 2–0 success over Espanyol at the RCDE Stadium.[17]
On 19 September 2020, Reguilón joined Tottenham Hotspur on a five-year deal[19][20] with a reported £27.5m buy-back clause.[21] He made his debut on 29 September 2020, in the home game against Chelsea in the fourth round of the League Cup, in which he assisted teammate Erik Lamela's equalising goal, which was then followed by a penalty shootout. Spurs won 5–4 on penalties putting them through to the next round of the competition.[22] He made his Premier League debut on 4 October, in a 6–1 win away to Manchester United.[23] On 19 May 2021, Reguilón scored his first goal for Tottenham − the winning goal in a 2–1 Premier League victory over Leeds United.[24]
Loans to Atlético Madrid, Manchester United and Brentford
On 30 August 2022, Reguilón joined Atlético Madrid on loan until the end of the season.[25] Upon returning to Tottenham, he joined Manchester United on a six-month loan on 1 September 2023 as emergency cover for the injured left-backs Luke Shaw and Tyrell Malacia.[26] He returned to Tottenham on 2 January 2024, following the activation of a break clause within the loan agreement, as Shaw had by then recovered from injury.[27]
Two weeks later, on 17 January 2024, Tottenham loaned Reguilón to fellow Premier League side Brentford until the end of the season.[28]
^Rodríguez, José María (22 December 2018). "El Madrid agranda su leyenda" [Madrid largen their legend]. Marca (in Spanish). Retrieved 22 December 2018.
