Everyone knows how Cuper lost 3 European finals in a row and the Scudetto with Inter and that has him labeled a loser. However, there is an untold story about another one who repeatedly managed to snatch defeat from the jaws of victory and that is Ancelotti. Let's take a look at his record.
1) Champions League semis 1998/99 Juve-Man United: has 1-1 from the first leg, plays the second leg at home, Juve take a 2-0 lead within 15 minutes and ends up losing 3-2.
2) Serie A 1999/2000: throws away a 9 point lead with 7 games to go and the Scudetto goes to Lazio!
3) Serie A 2000/2001: Championship decider Juve-Roma, Juve takes 2-0 lead after 10 minutes, holds it until 82nd but it ends 2-2.
4) Coppa Italia final 2002/2003: beats Roma 4-1 in Olimpico in the first leg. In the second Roma take a 2-0 lead but Milan claws back to 2-2 without even them knowing how.
5) Champions League QF 2003/2004: Throws away 4-1 from the first leg against Deportivo by losing 4-0 in the return.
6) Champions League SF 2004/2005: Throws away 2-0 from the first leg against PSV and only the passivity of the opponent allows them to pass.
The only time he did win something was when his direct competitors were even bigger losers: Roma in Serie A and Juve in CL(lost 5 finals, along with Benfica, more then any other team).
So there you have it, facts have spoken.