The stopper has been a one club man having played all his career at Milan. The former Italian international has seen everything in Calcio and he has come up against some tough opponents since making his debut in 1985.
Maldini admits that two of the games greatest ever players were the toughest he has come up against during his playing days at San Siro.
"The best ever I played against was Maradona," Maldini told Sky Sport Italia.
"He is the striker who has put me in the most difficulty on the pitch. The best is Maradona but even Ronaldo during his first two years at Inter was a phenomenon.
"The best derby? Probably the one in 2003 in the Champions League. That was the most intense as it seemed as if we were playing for days."
The Italian also had some words on Andriy Shevchenko and his recent return to form after his poor stint at Chelsea. Il Captiano believes the hit-man always wanted to return from the moment he left San Siro.
"When he arrived at first he was already a champion," the defender said.
"The club made a heavy investment and he scored lots of goals, he was one of the best buys ever.
"His return? I think he always wanted to come back and he did it all himself. He told everyone that he wanted to return. His come back is like a victory for him and us."
Maldini's Milan travel to Cagliari on Sunday night and they will be hoping for a positive result following their recent return to form.