On 24 May 2018, Pochettino signed a new five-year contract to keep him at Tottenham until 2023. In December 2018, Pochettino won his 100th Premier League match as manager of Tottenham after a late win against Burnley; he became the first Tottenham manager to reach this milestone and the third quickest Premier League manager to achieve the feat with a single club. On 8 May 2019, Pochettino led Tottenham to their first ever Champions League/European Cup final after beating Ajax on away goals (3–3 aggregate), with his side coming back from a 2–0 deficit (3–0 aggregate) at half-time in Amsterdam, only for Lucas Moura to score a second-half hat-trick. The final in Madrid ended in a 2–0 defeat to Liverpool.