Tottenham Hotspur secured a famous Champions League victory on a wet night in Milan.
The visitors matched their illustrious opponenents throughout the clash, and grabbed a winner on 80 minutes when Peter Crouch slotted home from a rapid Aaron Lennon breakaway.
Harry Redknapp's men shaded the first half at the San Siro as Milan struggled to get out of the blocks. Chances were at a premium though, with Rafael Van der Vaart's deflected shot as close as the visitors came midway through the period.
Robinho flashed wide on the stroke of half-time, but the game would get much better after the break.
Milan started to build up pressure, with Heurelho Gomes making two fantastic saves from Mario Yepes to keep Spurs in the tie.
The introduction of Luka Modric appeared to lift the visitors, and with ten minutes remaining Crouch grabbed the winner after a classic fast counter.
Michael Dawson and William Gallas produced a sterling perofrmance at the back throughout, and it was Dawson who was fouled in injury-time as Zlatan Ibrahimovic's overhead kick was correctly ruled out.
There was controversy after the whistle too, with Gennaro Gattuso squaring up to Spurs assistant Joe Jordan for the second time. He was booked earlier in the game, and will miss the second leg.