1990/91 was a rare, trophy-less season for Maldini and Milan, but normal service was resumed the following season when Maldini helped them to another Serie A title, quickly followed by another a year on.
In the midst of this, Milan went on a 58-match unbeaten run in Serie A, which is a record which still stands to this day. As well as being a record in Italian football history, that unbeaten run is the third longest in any top flight European league.
1993/94 was really Maldini's season, however. His classy defending and unparalleled ability to read the game lead Milan to a third consecutive league title, and they completed a historic double by claiming their fifth European Cup, the third in Maldini's time there.
The 1994 World Cup was where Maldini really shone, guiding Italy to the final against Brazil. He kept the likes of Romario and Bebeto out for 120 minutes as it ended 0-0, and went to penalties.
Brazil ended up winning after Roberto Baggio ballooned the crucial penalty over the bar. Once again, the most coveted prize in the game had eluded Paolo Maldini.
But, to help him get over this crushing disappointment, he received the highest accolade a footballing individual can get: the World Player of the Year award and, in doing so, he became the first defender to win such an award. Not even the likes of Bobby Moore or Franz Beckenbauer had won that award.
After former Italy captain Franco Baresi had announced his retirement following Italy's World Cup final loss, the armband was given to the 26-year-old Maldini.
As the Milan "Dream Team" started to break up, 1994/95 was another trophy-less season, but the very next year, the "Dream Team" had one final hurrah as they won the league title for the fourth time in six years.
Silverware became increasingly rare over the next few seasons, with only one Serie A title to show for their efforts between 1996 and 2002.
It was in 2002 that Maldini led Italy into the World Cup and, after crashing out in the quarter-finals in 1998 to hosts and eventual winners France, Maldini made it clear that the tournament would bring the curtain down on his remarkable international career.
It wasn't to be a fairy-tale ending, however, as Italy were beaten in the second round, again by the hosts, this time losing out to South Korea after extra time.
True to his word, Maldini retired after that game. He left the Italian national team as the most capped player in their history, with 126, and he also recorded the most caps as captain, leading his country on 74 occasions.
2003 saw the return to winning ways for Milan and Maldini as, for the first time in his Milan career, Maldini tasted success in the Italian Cup. That wasn't the highlight of there season, however, as they also won the Champions League, beating Juventus in the first ever all-Italian final on penalties, to claim their sixth title.
The following season saw Maldini help Milan to another Serie A title, the seventh Maldini had won in his career.
Then, the season after that, he helped Milan to yet another Champions League final, this time against Liverpool. Maldini scored the fastest goal ever in a Champions League final (51 seconds), and became the oldest ever Champions League final scorer.
Despite being 3-0 up at half-time, however, Liverpool staged a remarkable comeback to win on penalties in what Maldini later described as the worst moment of his career.
He had a chance to exact revenge two years later, however, as the two once again met in the Champions League final. This time, Maldini's Milan came out on top, giving Maldini his fifth European Cup/Champions League winners medal.
Maldini has recently signed a new one year deal, despite now being over 40 years old. His loyalty, dedication and fitness are perhaps unbeaten in footballing history.
With 878 games played for Milan, and 126 for Italy, Maldini is one of a handful of players to have played over 1000 competitive games.
He certainly must be considered among the greatest players to ever walk this planet, and when he finally does decide to hang up his boots, it will be the end of an era for world football.
This has been a tribute to Paolo Maldini.
Click here to see other tributes made by this author.
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