The 33-year-old, currently in his second spell with Serie A club Sampdoria, described his perfect night as "sex and then food" in his autobiography, Dico Tutto, an assessment he has since loosened to include football.
"Perfect! Those are the best things," Cassano told AS. "Until February 2, 2008 eh? Then I met my wife. But until then, yes."
The former Roma, Inter and Milan star played for Los Blancos between 2006 and 2008 and says his status in Madrid helped him satisfy his addiction.
"When you’re 20 and like girls, there’s a force that allows you to do it every day," he said. "And I had the chance! Cassano was a Madrid player! If I had done anything else, no-one would have looked at me... like my mother! I’m good, but I’m not handsome."
Cassano says the first 16 years of his life were "a total disaster" and admits that he was viewed as a "rebel" or "madman" in the early stages of his career, but insists he is happy.
"On the eve of a 4-0 win over Juventus, I stole the keys to Trigoria and came back at six o'clock in the morning," he confessed. "I had my best night on the pitch, I won a penalty and scored two goals."