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.

11 November 2008 - Real Madrid Gets Romo'd

On 11 November 2008, Spanish third division side Real Unión Club de Irún lost away to Real Madrid, 3-4, in the Round of 32 of the Copa del Rey. Thanks to their 3-2 win in the first leg, however, Irún advanced on an aggregate 6-6 score with a 3-2 advantage in away goals.

Irún had already been tested in the cup with early-round wins over CD Lugo (0-3), UE Sant Andreu (2-1), and Barakaldo CF (2-1). Real Madrid, on the other hand, was playing their first match of the tournament, entering the competition in the Fourth Round.

The match was even at 2-2 in the second half, when Real Madrid substitute Alberto Bueno put his team ahead with a goal in the 69th minute. Real Madrid captain Raúl appeared to secure the Blancos' advancement with an 85th-minute strike--his third of the match--but a defensive miscue gave Irún another chance and midfielder Arangoa Eneko Romo scored the decisive goal in the 90th minute.

It was the first time in Real Madrid's history that they were eliminated by a third division side at home. History soon repeated itself, however, as the Blancos were eliminated from the 2009-10 Copa del Rey in the Fourth Round by third division side AD Alcorcón.

Irún's moment of glory was fleeting, as they were eliminated by Real Betis in the Fifth Round, 2-0. In 2009, they were knocked out in the Second Round by second division side RC Celta de Vigo, 2-1.