Some 24 years since that January day in 1985 against Udinese, Maldini will finally hang up his boots in the season-ender at Fiorentina on Sunday having broken almost every appearance record available.
However, the 40-year-old's haul of 126 Italy caps, seven Italian titles and five European Cups is not just because he has been around so long. It is also because he was one of the best.
"I am proud of how people see me," he said this week. "I have given everything for the Rossoneri shirt."
A fearless yet stylish defender, who switched effortlessly between left back and central defence, Maldini would walk into most people's greatest ever World Select XI.
Even his last ditch tackles were elegant while he rarely looked harried and often left attackers looking foolish.
To stay at one club all his life is also a tremendous achievement which few peers have managed.
His father Cesare enrolled Paolo into Milan's youth ranks and from that point on he was never leaving.
His bond is so strong with Milan that his son Christian is now following his father's footsteps in the academy.
Despite all the trophies and fans, including many female admirers, Maldini will harbour some regrets.
He quit the Italy team in 2002 after a World Cup second round defeat to South Korea where he had been outjumped by Ahn Jung-hwan for the hosts' extra-time winner.
RIGHT TIME
He never won a trophy with Italy but felt it was the right time to retire from international football as the Azzurri's most capped player.
Four years later, though, he had to watch on as his former team mates lifted the World Cup against the odds.
Maldini would have quit last season had Milan won back-to-back European Cups. He yearned to finish his career with a ninth final and the chance of a sixth winners' medal.
Defeat by Arsenal in the Champions League first knockout round in March 2008 robbed him of that dream with Milan also failing to qualify for the 2009 competition after finishing a poor fifth in Serie A.
His record of eight finals will have to be shared with Real Madrid's Francisco Gento.
A stuttering finish in the league this term, with Milan battling Fiorentina for the final automatic Champions League spot, is not how he would have liked to bow out.
Some ultra fans also unveiled banners critical of him at his San Siro farewell in the defeat against AS Roma last Sunday.
Despite this and his wish not to immediately enter management, it seems certain Maldini will still be at Milan in some role for many more years to come.
"Nothing has been sorted. I need a holiday," he said.
