Manchester City have become accustomed to Champions League heartache, but the manner of their latest collapse against Real Madrid might be the most painful defeat of all. Four times Pep Guardiola’s men held a two-goal advantage in a classic semi-final tie they eventually lost 6-5 on aggregate.

Thirteen-time champions Madrid somehow found a way to win as City, last year’s defeated finalists, melted away in the white-hot atmosphere of the Santiago Bernabeu on Wednesday.

For 89 minutes, the English champions showed the maturity built up over a decade of experience in the competition but in 90 seconds their best-laid plans were destroyed. Riyad Mahrez’s stunning strike 17 minutes from time put the visitors 1-0 up on the night and 5-3 on aggregate, apparently ending the contest.

Madrid had not even mustered a shot on target until Rodrygo swept home Karim Benzema’s cross as stoppage time approached. Suddenly, the Bernabeu believed and yet another of the world’s most expensively assembled squads succumbed to the Real rope-a-dope just as Paris Saint-Germain and Chelsea had done in the previous two rounds.

Rodrygo headed in again after less than a minute of the six added on and could even have had a hat-trick before extra-time started.

In the end, fittingly, it was Benzema who delivered the final blow from the penalty spot to earn an unlikely victory in a tie in which Madrid had trailed for 178 minutes. It was a case of history repeating itself, both in terms of the Madrid fightback and also a Guardiola team failing to negotiate the fine margins that define the latter stages of the Champions League.

Near misses

It is now 11 years since he won the second of his two European Cups as a coach at Barcelona. In the 10 seasons he has been in charge of Barca, Bayern Munich and City since, he has lost a final — last year’s 1-0 defeat to Chelsea, five semi-finals and three quarter-finals.

“Always I had defeats so tough in the Champions League,” said the 51-year-old. “It’s tough for us, we cannot deny it, we were so close to a Champions League final.”

City, who have never been crowned European champions, will have another go next season, possibly armed with the extra artillery of Erling Haaland, with reports suggesting the Norwegian will move to the Etihad from Borussia Dortmund. Before then, Guardiola must rouse a group of mentally and physically exhausted players to avoid ending the season without a trophy for the first time since the 2016/17 campaign.

City hold a one-point lead over rampant Liverpool — who reached the Champions League final by beating Villarreal, at the top of the Premier League with four games to go.

“We need time now,” admitted Guardiola, whose side host Newcastle on Sunday, a day after Liverpool play Tottenham. “One or two days but we will rise, we have to do it.

“The players gave everything. We were so close but in the end we could not do it.”

A much-anticipated clash between England’s top two teams will now not take place in Paris on May 28, with Liverpool instead facing Madrid for the third time in a European Cup final. But it is still in City’s hands to deny the Reds a historic quadruple.

Win their final four games and Guardiola will claim a 10th league title in 13 seasons at Barca, Bayern and City. That record is what makes the Catalan coach one of the most revered of all time. But the trophy he and City were brought together to win remains out of reach.

Despite the huge sums invested by their Abu Dhabi-based owners, the club cannot buy the belief that decades of Champions League success has brought to both Madrid and Liverpool.

Real go for European Cup number 14 in Paris, while Liverpool would join AC Milan as the second most successful club in the competition’s history on seven titles with victory at the Stade de France. City would be delighted with just one.