Carlo Ancelotti became the first manager in history to reach five Champions League finals after Real Madrid stunningly beat Man City 6-5 on aggregate to set up a match with Liverpool.
The 62-year-old is already the first man to lead four different clubs to the Champions League semi-finals, and after a stunning extra-time comeback win over City at the Bernabeu on Wednesday, now stands alone as the only man in history to manage in five Champions League finals.
Plus, Real Madrid's 4-0 win over Espanyol on Saturday put him alone in managerial history in leading teams from Serie A, the Premier League, Ligue 1, the Bundesliga and La Liga to league titles.
He was victorious in his first Champions League final with a penalty shoot-out win over Juventus at Old Trafford in 2003, but two years later was beaten on spot kicks after a stunning comeback from Liverpool in Turkey. Another two years on and he got his revenge, as Milan beat the Reds 2-1 in Athens.
Despite his close and long-term relationship with the city of Milan, perhaps his best final was saved for his first spell at the Bernabeu, where he finally helped Real Madrid to 'La Decima', their 10th Champions League trophy, an achievement they had waited 12 years to realise.
Eight years on from last lifting the European Cup, he will now have the chance to add a fourth winners' medal to his collection when Real take on Liverpool in Paris later this month - with Klopp taking to the dugout in his fourth final, only one behind Ancelotti.
Carlo Ancelotti: Champions League final record
2003: AC Milan beat Juventus 3-2 on penalties - Won
2005: Liverpool beat AC Milan 3-2 on penalties - Lost
2007: AC Milan beat Liverpool 2-1 - Won
2014: Real Madrid beat Atletico Madrid 4-1 - Won
2022: Real Madrid v Liverpool (May 28th) - tbc