#4 Carlo Ancelotti: Real Madrid 0-4 Atletico Madrid
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The three-time Champions League winner is one of the most travelled and well-respected managers in the world of football, having won league trophies in England, France and Italy in addition to a number of cup competitions. However, one place he failed to win the league was Spain, where he managed Real Madrid from 2013 to 2015 with a solitary Copa Del Rey added to the trophy cabinet in terms of domestic success.
Rubbing salt into his wound in the latter of the two seasons were cross-town rivals and reigning champions Atletico Madrid who beat them 4-0 in February 2015 at the Vicente Calderon - prompting Ancelotti to say it was the worst result of his career. And it really stung when Real lost the title race to Barcelona by just 2 points.
It was actually the fifth time Ancelotti had lost a game 4-0 in his career, thrice with AC Milan and once with Juventus, but perhaps the most disappointing of all would have been the Champions League final of 2005 where Milan blew a 3-0 lead at half-time against Liverpool.
