The two coaches experienced a remarkable reversal of fortunes in the final minutes at the Bernabeu as Madrid sneaked victory
Both Carlo Ancelotti and Pep Guardiola made Champions League history in Wednesday's thrilling Champions League semi-final decider, though the Manchester City boss will most likely not be amused at his new place in the record books.
City looked destined for the final going into injury time against Real Madrid, leading 5-3 on aggregate after Riyad Mahrez had widened their first-leg advantage in the Bernabeu.
But Ancelotti and Madrid had other ideas, netting twice at the death through Rodrygo before this season's hero Karim Benzema decided the tie in extra time from the penalty spot.
Ancelotti sets new competition best
On Saturday the Italian broke new ground in European football, winning La Liga with Madrid to complete the first-ever coaching clean sweep of the continent's top five leagues.
Ancelotti, though, also thrives in the Champions League, where he enjoys an almost unprecedented level of success.
Wednesday's victory sealed his fifth appearance in the competition's final, having taken Milan to that stage in 2003, 2005 and 2007 before leading Madrid to the decider in his first spell at the Bernabeu back in 2014.
No other coach has managed that number - though Liverpool might take some heart from the fact that they inflicted his only final defeat to date from his previous four visits, in the 2005 showpiece.
"I can't say we're used to living this kind of night. It happened for us what happened against Chelsea. Really difficult to say why," Ancelotti told BT Sport after the game.
"This is the biggest history of this club that helps us to kick on when it seems we are gone."
"It's true, the game was close to finishing, we were unable to find the last energy we had. We played a good game against a strong rival. After that we equalised, of course we were better psychologically in extra time.
"I have no time to think about this [that the game was lost], it was difficult in this period when City had good control of the game. The last opportunity we were able to go to extra time."
More Champions League woe for Pep
Guardiola, meanwhile, despite being a two-time Champions League winner as a coach, has endured nothing but disappointment in the competition in recent years.
This marks his sixth semi-final elimination, a record he now shares with Jose Mourinho and not one he will wish to crow about.
Benxe
503
May your ex come back like the way Real Madrid came back against Man City, Amen!🙏🏾
RaghibMustafa
435
Madrid and Liverpool be like...
stoner02
430
Real Madrid are going to Paris for the UCL trophy and Kylian Mbappe
JoyNg
348
The Great Don🔥🔥🔥 Respect👏👏👏
fan4ever
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Benzema ties Ronaldo for most Goals in a Single [KO] stage 1️⃣0️⃣ 🤯🔥
KHMMURU07
233
Pep be like Shiekh i need 2 billion in transfer summer 😂🏳
Lunacdlstz
203
carlo anceloti's substitute is underrated
Papajoe1
89
Is this actually working, I've been thinking