Maldini stepped onto the court at the Milan challenger event as its most decorated sportsman.
But the 49-year-old Italian football legend -- whose tennis dream was to "play against Roger Federer" -- saw his career hopes dashed with a chastening defeat to doubles specialists David Pel and Tomasz Bednarek while playing alongside his tennis coach Stefano Landonio.
It was a logical defeat, given the players' ranking history. Dutchman Pel is ranked 208th in the world while Poland's Bednarek reached a career high of 44th in 2014, reaching a quarter-final at Roland Garros on the way. Landonio's highest ever ranking was 975th, in 1996.
Maldini and Landonio were given an invite to the event thanks to their recent victory in an amateur tournament.
But although the Challenger circuit is one level below the elite ATP circuit played by the likes of Federer, it proved a step too far for Maldini and his partner.
Maldini produced a few strong forehands, but showed flaws in his backhand and was well below professional standard on serve.
It was over within an hour, and Maldini said that, as far as his professional tennis career is concerned, it is game, set and match. "It was a great experience and one I really enjoyed, but I won't repeat it," said Maldini, who can nevertheless afford to regard it as a blip in an otherwise sterling career.
A true legend in Italy, and indeed throughout the footballing world, Maldini won 26 trophies with Milan, playing a record 647 matches in Serie A, and won five European Cups on the way.
Maldini earned 126 caps for Italy and was a finalist at both the 1994 World Cup and Euro 2000. He is currently technical director at Miami FC, who play in the NASL, the American second division below Major League Soccer.