Tottenham had a magnificent result in the San Siro were, after a shading the first half, they defended in depth after the break and scored the only goal through Peter Crouch with ten minutes remaining.
Milan qualified for the knockout stage with the lowest number of points and scored the joint fewest goals in progressing, whilst their Premier League visitor’s Spurs were the joint leading scorers in the group stage.
And it was this ability to score that proved decisive ten minutes from time as Aaron Lennon broke quickly with pace setting up Crouch for an easy finish.
Spurs had keeper Heurelho Gomes to thank for keeping them in the tie as Milan turned up the pressure in the second half.
The Brazilian stopper made two superb saves from Mario Yepes headers.
In a dramatic end to the game Zlatan Ibrahimovic had a late goal disallowed for Milan and tempers flared at the end with clashes between the Italians and the visitor’s bench - Gennaro Gattuso appearing to headbutt Tottenham assistant manager Joe Jordan after the final whistle.
Not that Spurs boss Harry Redknapp will mind as he contemplates taking a narrow advantage back to White Hart Lane for the second leg.
Referee: Stéphane Lannoy (France)
Venue: San Siro Stadium
32 Abbiati (Amelia 18)
33 Thiago Silva
76 Yepes (yellow card)
08 Gattuso (yellow card)
10 Seedorf (Alexandre Pato 46)
16 Flamini (yellow card)
07 Alexandre Pato
22 Corluka (Woodgate 59)
11 Van der Vaart (Modric 62)
40 Pienaar (Kranjcar 76)