The previous season the club had obtained the Scudetto for the first time in their history thanks to the little Argentine's magic, and Maldini and Maradona went on to face each other numerous times at club and international level over the years.
More than a decade later, the left-back then had the privilege of tussling with Brazil idol Ronaldo in his twilight years, as he continued to star for Milan well into the 21st century with the Brazilian lining up at eternal rivals Inter.
"I was lucky enough to play against Maradona. He and Ronaldo, when he was at Inter Milan - they were my toughest opponents," Maldini explained in an interview with Bild.
Maldini played under the likes of Arrigo Sacchi and Carlo Ancelotti at San Siro, in an incredible 24-year career that saw him play over 900 games for his boyhood club.
And he had no hesitation in naming two other former Serie A rivals as the best of the current generation of coaches - although Liverpool's Jurgen Klopp also received a mention.
"The best coach right now? Hard to say. There are many good ones - like Diego Simeone. Maybe Zinedine Zidane, but he still lacks experience. I also like what Jürgen Klopp does in Liverpool and how he made Dortmund play."