AC Milan failed to produce the flair that made them seven-times European champions and were eliminated from the Champions League by Tottenham Hotspur after a 0-0 draw put the English side through 1-0 on Wednesday.
Spurs advanced to the quarter-finals after another night of unrelenting tension at White Hart Lane and the London club's unlikely adventure among Europe's elite continued.
Milan's big-name players like Zlatan Ibrahimovic, Robinho, Alexandre Pato and the evergreen Clarence Seedorf fought non-stop but despite creating the better chances they failed to make the last eight for the fourth successive season.
Spurs, who won 1-0 at the San Siro with a late Peter Crouch goal, could not press home their advantage but the Premier League side gave a resolute defensive performance to reach the quarter-finals of Europe's premier competition for the first time since getting to the European Cup semis in 1962.
"It's a fantastic achievement for this club, playing in the Champions League for the first time in our history. To have beaten Inter Milan in the group stage and now AC Milan, well anything else is a bonus now, just being in the Champions League is a bonus," Spurs manager Harry Redknapp told reporters.
Milan coach Massimiliano Allegri said he was "very very disappointed" his side lost. "I thought we played very well, we made all the chances.”