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Featured Image Credit: PA
The 52-year-old legendary defender spent his entire club playing career at AC Milan and captured an abundance of silverware during his time at the San Siro.
But Maldini, who is regarded as one of the best defenders of all time, faced his fair share of legendary opposition that caused him problems on the pitch.
The former Italy international called iconic Brazilian Ronaldo "phenomenal" during his time at Inter Milan.
Maldini told Italian newspaper Gazzetta dello Sport: "My toughest opponents would be Diego Maradona, Ronaldo, who was phenomenal in his two years at Inter, and Zinedine Zidane."
The Italian legend, who made over 600 appearances for Milan, won an incredible seven Serie A titles before he retired from football in 2009.
Former Barcelona and Inter striker Ronaldo previously praised the brilliance of Maldini as he hailed him as the toughest player he faced in his illustrious playing career.
"Toughest defender I've faced in my career? Paolo Maldini would be the toughest ever," he said.
"Among other Italian defenders, I would say [Fabio] Cannavaro, [Alessandro] Nesta and [Pietro] Vierchowod, all of which were very strong."
Ronaldinho echoed his former Brazil teammate's sentiments over Maldini as he said it is "impossible not to be amazed by how he made it all look effortless."
The 40-year-old explained: "It has to be [Paolo] Maldini. Too many skills.
"It is impossible not to be amazed by how he made it all look effortless, especially when you get to play with him."