The 2022/23 Champions League semifinals have drawn up two crunch pairings, including a San Siro battle between AC Milan and Inter Milan, and a reunion for Manchester City and Real Madrid.
The two sides met at the same stage last season, as Carlo Ancelotti's side got the better of Pep Guardiola's team, following a dramatic extra time win in Madrid.
The two clashes in 2021/22 demonstrated both manager's strengths in Champions League action with Ancelotti's calm experience eventually proving to be a clinching factor.
Another meeting in 2023 will be decisive for both managers, with Guardiola pushing to win a first European title at City, and Ancelotti under pressure, after failing to defend his La Liga crown this season.
MORE: How many trophies has Carlo Ancelotti won? Contract, salary, and more on Real Madrid boss
Pep Guardiola vs Carlo Ancelotti head-to-head history
Despite their incredible respective records across domestic and Champions League action, Guardiola and Ancelotti have only faced each four times in the competition.
Ancelotti won both of their clashes during Guardiola's time at Bayern Munich, and his first stint in Madrid, before getting the better of him again last season.
However, the majority of their battles came during Ancelotti time at Everton, where Guardiola won four from four across the Premier League and FA Cup.
*Data correct as of May 8, 2023
Pep Guardiola vs Carlo Ancelotti head-to-head
| Season | Competition | Stage | Final Result | Scorers |
| 2013/14 | Champions League | Semifinal | Real Madrid 1 Bayern Munich 0 | Benzema |
| 2013/14 | Champions League | Semifinal | Bayern Munich 0 Real Madrid 4 | Ramos x2, Ronaldo x2 |
| 2019/20 | Premier League | - | Manchester City 2 Everton 1 | Jesus x2, Richarlison |
| 2020/21 | Premier League | - | Everton 1 Manchester City 3 | Richarlison; Foden, Mahrez, Silva |
| 2020/21 | FA Cup | Quarterfinal | Everton 0 Manchester City 2 | Gundogan, De Bruyne |
| 2020/21 | Premier League | - | Manchester City 5 Everton 0 | De Bruyne, Jesus, Foden, Aguero x2 |
| 2021/22 | Champions League | Semifinal | Manchester City 4 Real Madrid 3 | De Bruyne, Jesus, Foden, Silva; Benzema x2, Vinicius Jr |
| 2021/22 | Champions League | Semifinal | Real Madrid 3 Manchester City 1 | Rodrygo x2, Benzema; Mahrez |
Pep Guardiola vs Carlo Ancelotti in UEFA Champions League
Ancelotti's final win over Liverpool in 2023 crowned the Italian as the most successful manager in European Cup/Champions League history, with four titles.
The 63-year-old won two Champions Leagues during his time with AC Milan and two at Real Madrid, in 2014 and 2022.
Guardiola has two titles, both won at Barcelona, in 2009 and 2011.
*Data correct as of May 8, 2023
Pep Guardiola vs Carlo Ancelotti Champions League manager record
| Pep Guardiola | Carlo Ancelotti | |
| Champions League games | 158 | 189 |
| Champions League wins | 99 | 108 |
| Champions League draws | 33 | 40 |
| Champions League losses | 26 | 41 |
| Finals reached | 3 | 5 |
| Titles won | 2 | 4 |