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.
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.
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.
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.
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.
His record of eight finals will have to be shared with Real Madrid's Francisco Gento.
"Nothing has been sorted. I need a holiday," he said.
