(CNN) -- A late goal from Peter Crouch stunned seven-time European champions AC Milan as Tottenham Hotspur secured a 1-0 win in the San Siro on Tuesday night.
Crouch converted after a brilliant run from fellow England international Aaron Lennon to give Tottenham a precious lead for their home tie of the Champions League last 16 knockout tie.
Earlier in the second half, Tottenham goalkeeper Heurelho Gomes produced two wonder saves to keep AC Milan at bay, both from Mario Yepes.
First, the Brazilian stretched to palm over a header which looked destined for the top corner and then repeated the trick from another fierce header which he pushed out.
After Crouch's 80th minute goal, Milan went in desperate search of an equalizer and Robinho's close range effort was blocked by the excellent Michael Dawson.
Deep into injury time, Milan thought they had equalized through a Zlatan Ibrahimovic overhead kick, but the Swedish striker had pushed Dawson and it was ruled out.
At the final whistle there were unsavory scenes as Milan midfielder Gennaro Gatusso clashed with Tottenham assistant coach Joe Jordan, headbutting the former Scottish international.
The two had earlier exchanged words after former Arsenal star Mathieu Flamini was yellow carded for an ugly two-footed challenge on Vedran Corluka which left the Tottenham defender on crutches.
He was replaced by Jonathan Woodgate, making his first appearance after a lengthy injury layoff.
Gatusso, who had earlier been booked, will miss the second leg but could be punished further by UEFA for the incident which was captured on television.
Jubilant Tottenham manager Harry Redknapp said all his players had contributed to the famous victory.
"The whole team were magnificent, everyone did their job tonight, it was a great night for Tottenham," he told Sky Sports.
Tottenham had the better of the first half with the home side handicapped by the loss of goalkeeper Christian Abbiati, who was taken to hospital with a head injury after being stretchered off after a awkward fall.
Milan coach Massimiliano Allegri replaced him with Marco Amelia and he was kept the busier of the two goalkeepers.
Early in the second half, Amelia could only watch as a Rafael van der Vaart chip went narrowly side, but then Milan, sparked by the introduction of Pato, at last began to show the form which has taken them top of Serie A this season.
Tuesday's other first leg tie saw veteran Spain striker Raul return to Spain with his new German side Schalke and score a vital equalizer in the 1-1 draw against Valencia.
Roberto Soldado's sixth Champions League goal put Valencia ahead on 17 minutes in the Mestella, but 33-year-old veteran Raul, who moved to Schalke from Real Madrid in the summer, leveled on 64 minutes.
Raul is the all-time leading scorer in the Champions League and the away goal is one of his most valuable ahead of the second leg in Gelsenkirchen on March 9.
Schalke's draw was only spoiled by a late sending off for Lukas Schmitz but they held on with 10 men.
