The 2018/19 season was one of the most emotionally intense campaigns in the modern history of Tottenham Hotspur.

Under Mauricio Pochettino, Spurs had firmly established themselves as a top-four Premier League side, and with their long-awaited move to the new Tottenham Hotspur Stadium on the horizon, the club found itself making a deep run in the UEFA Champions League as the season reached its decisive stages.

After comfortably overcoming Borussia Dortmund in the Round of 16, Tottenham were drawn against domestic rivals Manchester City, managed by Pep Guardiola, in the quarter-finals. A potential semi-final clash with Ajax and an all-English final against Liverpool awaited if they progressed.

For Pochettino, Lucas Moura’s unforgettable hat-trick against Ajax remains one of the defining moments of his managerial career. However, he is quick to point out that the road to that night in Amsterdam began with the hard-fought battles against Manchester City.

“That match against Ajax was one of the greatest nights of my career, but without the previous tie against City, we wouldn’t have reached that semi-final,” Pochettino told FourFourTwo.

He recalled, “We won the first leg 1-0 at home against City, in a match where Hugo Lloris saved a penalty from Sergio Aguero, and unfortunately, Harry Kane suffered an ankle injury.”

Pochettino added, “Guardiola had once referred to Tottenham as ‘Harry Kane’s team’, and that didn’t sit well with us because it seemed to overlook the contribution of the entire squad.”

“So going into the second leg at the Etihad Stadium without Harry and still managing to knock City out carried enormous emotional and sporting value for us.”

In Kane’s absence, Son Heung-min rose to the occasion with two goals, while Fernando Llorente’s crucial strike ultimately sealed Tottenham’s place in the semi-finals, as their 4-3 defeat on the night saw them advance on away goals.

Spurs then faced Ajax in the semi-finals, where they once again progressed on away goals thanks to Lucas Moura’s hat-trick heroics. That set up a final showdown against Liverpool, who had pulled off their own miracle by overturning a 3-0 first-leg deficit to eliminate Barcelona at Anfield.

In the final in Madrid, a second-minute penalty converted by Mohamed Salah and a late strike from Divock Origi ended Tottenham’s dream of capturing their first European title.

Reflecting on that night, Pochettino said, “We can’t have any regrets. We played the way we believed was best. After that, there are certain elements beyond your control.”

“That handball by Moussa Sissoko wouldn’t be given as a penalty under today’s rules, and it completely changed the flow of the match because it put us at a disadvantage right from the start.”