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. Serie A leaders AC Milan went down 1-0 on home soil to Tottenham in the first leg of this Champions League encounter.
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 Attendance: 80,000
AC Milan scorers: Tottenham scorers: Crouch 80
AC MILAN 32 Abbiati (Amelia 18) 13 Nesta 33 Thiago Silva 76 Yepes (yellow card) 08 Gattuso (yellow card) 10 Seedorf (Alexandre Pato 46) 16 Flamini (yellow card) 20 Abate 77 Antonini 11 Ibrahimovic 70 Robinho
Substitutes 01 Amelia, 15 Papaststhopoulos, 17 Oddo, 18 Jankulovski, 66 Legrottaglie, 52 Merkel, 07 Alexandre Pato
TOTTENHAM 01 Gomes 13 Gallas 20 Dawson 22 Corluka (Woodgate 59) 32 Assou-Ekotto 07 Lennon 11 Van der Vaart (Modric 62) 12 Palacios 30 Sandro 40 Pienaar (Kranjcar 76) 15 Crouch
Substitutes 23 Cudicini, 19 Bassong, 39 Woodgate, 14 Modric, 21 Kranjcar, 09 Pavlyuchenko, 18 Defoe