After missing each other in European competitions for 36 years, United and AC Milan were drawn together in the Champions League’s last 16 in 2004/05. The first leg in Manchester was a tense affair, one which had been billed as Jaap Stam’s return to Old Trafford, only for the Dutchman to pick up an injury in the warm-up. Without him, Carlo Ancelotti’s men still won 1-0, thanks to Hernan Crespo’s predatory finish. The Argentinian, on loan from Chelsea at the time, again proved to be the difference in the return leg, with the striker grabbing the only goal of the game and securing Milan’s place in the last four.
We were paired with the Italians again in Europe’s elite tournament just two years later. It was the third semi-final to be contested by the clubs and United were aiming to undo our wretched record against the Rossoneri. With superstars in both line-ups, Cristiano Ronaldo put Sir Alex Ferguson’s side ahead in the first leg, only for a Kaka brace to send us in at the break trailing. A Wayne Rooney double turned that around, with his second strike coming in injury time to seal a fantastic 3-2 victory. But again it wasn’t meant to be, as Milan triumphed 3-0 a few weeks later to progress to the 2006/07 final, where they would beat Liverpool 2-1 in Athens.