Pep Guardiola now shares a painful record with long-time adversary Jose Mourinho following Manchester City's latest dramatic Champions League exit.
The Premier League champions looked on course to book their place in a second consecutive final after Riyad Mahrez fired the visitors in front against Real Madrid on Wednesday night. However, a late double from Rodrygo sent the tie into extra-time, and Karim Benzema sent the La Liga winners through from the penalty spot.
It was an astonishing comeback which in some ways defied belief, with Carlo Ancelotti's side failing to register a shot on target until Rodrygo's first goal in the 90th minute. However, it is the latest Champions League turnaround seen at the Bernabeu this season, with Real coming from behind to knock out Paris Saint-Germain and Chelsea earlier in the competition.
The Champions League trophy is the one which continues to elude Guardiola with City, and the latest heartbreaking loss now puts him level with Mourinho for the most eliminations at the semi-final stage. It was the sixth time the former Barcelona and Bayern boss has stumbled in the last four of the competition, with his last triumph coming in 2011.
For City, it was the first time they had tasted defeat in the semi-final stage, with previous exits against the likes of Liverpool, Lyon and Tottenham coming in the last eight. For Guardiola, defeat in the final four is now all too common having exited the competition at that stage in all three seasons with Bayern.
Reflecting on the 3-1 defeat at the Bernabeu, two-time Champions League winner Guardiola told BT Sport: "In the first half we did not have [the] game, we were not good enough. But we did not suffer much After we scored the goal we were better. We found our tempo and our game and the players were comfortable.
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"It is not like in the last 10 minutes they attack and attack and you suffer. It didn't happen. They put a lot of players in the box, with Eder Militao, Rodrygo, Vinicius Junior, Karim Benzema and they put in crosses and scored two goals.
"We didn't play our best, but it is normal, a semi-final, the players feel the pressure and wanting to do it. Football is unpredictable, it is a game like this. We have to accept it."
The challenge now for City is to regroup and somehow shake off this disappointment with the Premier League title race set to go to the wire. Guardiola's side still hold a slender one-point lead over Liverpool with four matches remaining, while the Reds also have to prepare for the Champions League and FA Cup finals.
City host in-form Newcastle on Sunday, before facing successive away trips to Wolves and West Ham. The reigning champions then finish the season on home soil against Steven Gerrard's Aston Villa.
