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3) 2003 Champions League title
Forgotten by many because of it being a slightly boring Champions League final, Ancelotti’s winning his first Champions League trophy was most definitely one of the Italian’s most iconic moments in football.
Along the way to their Champions League win, they had to knock Bayern Munich out of one group, before facing and getting past Borussia Dortmund and Real Madrid. They would then defeat both Ajax and rivals Inter Milan in the next two stages, setting up their final with Juventus.
Milan deserved to win the final, having defended strongly, having a perfectly good goal disallowed and hitting the post subsequently. As a result, the match would be decided by efforts from the penalty spot and on this occasion, unlike 2005, Andriy Shevchenko scored the decisive penalty.
Furthermore, beating Juventus in the final meant they were defeating a team who had beaten them to the Serie A title, showing how tough it would have been to win this game, and how iconic this moment was for Ancelotti.
