Maldini, now working as a director at Miami FC, qualified by wild card in the doubles in the weekend long Aspria Tennis Cup, part of the challenger circuit, the level below the ATP.
"He's got a good service, he doesn't have a speciality shot but he has no weak points either," his partner and coach Stefano Landonio told local media.
Maldini won 26 trophies with AC Milan including five Champions Leagues before finally hanging up his boots in 2009 aged 41. He also played 126 times for Italy.