Carlo Ancelotti will be looking to win his 100th Champions League game when Real Madrid face RB Leipzig at the Santiago Bernabeu on Wednesday.
The Los Blancos boss is currently on 99 victories in the competition and a win against the German side would move him onto a century and see him become just the second manager after Sir Alex Ferguson (102) in the history of the European Cup to reach 100 successes.
Last season, Ancelotti became the most successful coach in the history of the competition after leading Real Madrid to success. The Italian has lifted the trophy on four occasions.
He lifted the trophy twice while at AC Milan (2003 and 2007) and twice with Real Madrid (2014 and 2022).
The 63-year-old has managed the likes of Juventus, AC Milan, Chelsea, Paris Saint-Germain, Bayern Munich and Napoli during a hugely successful career.
He was voted UEFA best manager twice (2002-03 and 2021-22 seasons), IFFHS best world manager (2007 and 2014), Serie A best manager (2001 and 2004) and
Ligue1 best manager (2012-13).
He won the Premier League twice with Chelsea and was named Premier League Best Manager of the Month four times during his time in England.
Ancelotti will now be looking to oversee a challenge for a 15th European Cup for Real Madrid, who opened their 2022-23 campaign with a 3-0 success over Celtic last week.