20 January 1985 - Maldini Joins The Family Business

On 20 January 1985, 16-year old defender Paolo Maldini made his first professional appearance, coming on as a second-half substitute for AC Milan. He would go on to become the club's all-time appearance leader with 902 matches.

Maldini was following in the footsteps of his father, Cesare, who played defense at Milan from 1954 to 1966, winning 4 Serie A titles and the 1963 European Cup. Paolo was born in 1968 and joined the Milan youth team at the age of 10. By 1985, he had earned a spot on the bench and then, in a match against Udinese, he took the pitch for the first time, coming on for the second half.

The match ended in a draw and was Maldini's only appearance that season. But he became an established starter at left back the next season, making a total of 40 appearances in all competitions. In his 25 seasons with the Rossoneri, they won 7 Scudettos and 5 European Cup/Champions League titles.

Although Maldini maintained an incredibly high performance level for his entire career, his annus miribilis came in 1993-94. That season, Milan won both Serie A and the Champions League, while Maldini advanced to the World Cup Final with Italy, losing to Brazil on penalties. For his performance, World Soccer Magazine named him the 1994 World Player of the Year, the first time the award went to a defender.

25 May 2005 - The Miracle Of Istanbul

On 25 May 2005, Liverpool won their fifth European Cup/Champions League trophy, coming back from a 3-0 deficit to beat AC Milan on penalties 3-3 (3-2) before a crowd of 70,000 at Istanbul's Atatürk Olympic Stadium.

The win salvaged an otherwise disappointing season for the Reds, who had finished the Premier League season in fifth place after an early FA Cup elimination and a loss to Chelsea in the League Cup Final. The win also allowed Liverpool to compete in the next season's Champions League - their fifth-place League finish was outside the four qualification spots, but UEFA granted them a special exemption to compete in 2005-06 as title holders.

Milan were favored to win and, true to form, took an early lead with a volley from captain Paolo Maldini after only 51 seconds (it was the fastest-ever goal in a European Cup/Champions League Final and made the 36-year old Maldini the competition's oldest-ever goalscorer). Liverpool attacked the Milan area, but were unable to break through the Italians' defense. Liverpool's efforts exposed them to a counter-attack, resulting in two more Milan goals before the break, both from Argentinian striker Hernán Crespo (38', 42'), on loan from Chelsea.

Milan's 3-0 lead looked insurmountable, but Liverpool renewed their pressure after the break. They played only three defenders in order to bolster their attack, which paid dividends when they scored three goals in a six-minute period (Gerrard 54', Šmicer 56', Alonso 60') to draw level. Despite Liverpool's weakened back line, Milan were unable to score and the match went to extra time, then to penalty kicks.

Milan went first in the shootout and missed their first two kicks - the first went over the bar, while the second was easily saved. Liverpool made their first two, but their third was saved, so that after four kicks, Liverpool were ahead 3-2. Milan's Ukrainian striker Andriy Shevchenko, who had scored the winning penalty in the 2003 Final, stepped up to take Milan's last kick, knowing that he needed to convert it in order to prevent Liverpool from winning. Unfortunately for Milan, he sent it right down the middle where it was saved by keeper Jerzy Dudek.

26 November 2003 - Milan's Maldini Makes His Mark

On 26 November 2003, Milan defeated Ajax 1-0 in a Champions League group stage match before a crowd of 50,000 at Ajax's Amsterdam ArenA. The match was the 100th European Cup/Champions League appearance for Milan defender Paolo Maldini and the fourth time the two teams had met in the Champions League in 2003.

Maldini signed with Milan as a youth player in 1978, then as a professional in 1984. He made his first European Cup appearance in the 1988-89 campaign, which saw Milan claim its third title in the competition. By November 2003, Milan and Maldini had claimed three more European Cup/Champions League trophies (1990, 1994, 2003).

Ajax and Milan had a long history together in the competition, dating back to the 1969 Final in which Milan beat the Dutch club 4-1. Ajax returned the favor in the 1995 Final with a 1-0 win over the Italians. The clubs met in the quarterfinals of the 2002-03 Champions League, with Milan emerging victorious by the aggregate score of 3-2.

Maldini's century match was the second leg of the 2003-04 group stage, with Milan having won the previous leg 1-0 at home. In Amsterdam, Ajax battled to 0-0 draw at the break, despite having had to withdraw their star forward Zlatan Ibrahimović in the 40th minute due to injury. In the 51st minute, Milan striker Andriy Shevchenko chested a Cafu pass in front of the goal and calmly put the ball into the net. Milan then held on for the 1-0 win.

Both Ajax and Milan lost their last group stage matches, Ajax to Brugge and Milan to Celta Vigo. Ajax's loss to Brugge dropped the Dutch club to the bottom of the table and out of the competition. Milan finished at the top of the table to advance to the knockout rounds where they successfully defended their title.