|Lennon ghosts past Yepes before squaring for Crouch to hit the winner on a famous night for Spurs [GALLO/GETTY]
The electric pace of Aaron Lennon set up Peter Crouch for a vital away goal as Tottenham Hotspur left the San Siro with a 1-0 win against AC Milan in the first leg of their European Champions League tie.
Crouch's 80th minute strike came after England teammate Lennon ran with the ball from his own half, skipped past Mario Yepes and squared for the lanky striker to slot unmarked past Marco Amelia.
"We were the better side and I just had to keep up with Azza (Lennon) and stick it in," Crouch said of his goal.
"We'll take it back to White Hart Lane now, but the job's not finished."
In Wednesday's other last 16 tie, Raul made a goalscoring return to Spain to earn Schalke a 1-1 draw at Valencia.
The former Real Madrid forward produced a trademark finish from close range to cancel out Roberto Soldado's early strike for Valencia and take his record Champions League goalscoring tally to 69.
Spurs, who lost 4-3 to Inter Milan at the San Siro in the group stage after fighting back from 4-0 down, dominated the first half but failed to find a way through the Milan defence.
The Italians improved following the introduction of Alexandre Pato as a second-half substitute and Spurs keeper Heurelho Gomes made two instinctive saves to keep out powerful headers from Colombian veteran Yepes.
Tottenham looked pleased to be heading for a draw before England winger Lennon burst into the Milan half and laid the ball off perfectly for the unmarked Crouch to score with a clinical low shot.
Mathieu Flamini was lucky not to be sent off for a two-footed challenge that forced Vedran Corluka off injured in a tackle that Spurs boss Harry Redknapp described as a "dangerous, dangerous challenge" as he watched it on a Sky Sports replay afterwards.
Milan's Gennaro Gattuso was shown on TV headbutting Spurs assistant coach Joe Jordan after Zlatan Ibrahimovic had a last-minute equaliser ruled out.
"There's only one winner there - I've got my money on Joe," Redknapp said.
"Of all the people to pick on, don't pick on Joe."
The Premier League side bossed the early exchanges amid heavy rain inside the San Siro cauldron and had an early shout for a penalty turned down when the fit-again Rafael van der Vaart's effort appeared to strike Alessandro Nesta on the arm.
Crouch and Lennon caused seven-times winners Milan all sorts of problems and the Serie A leaders lost goalkeeper Christian Abbiati after 18 minutes with a head injury.
He could miss the second leg in London on March 9.
Abbiati went to hospital for checks on concussion and his replacement Amelia had to touch a fierce Van der Vaart shot over the bar.
Milan boss Massimiliano Allegri, with several midfielders such as Andrea Pirlo injured and the likes of Antonio Cassano ineligible, sent out a defensive-looking team with centre back Thiago Silva in midfield and in the first half it showed.
But the hosts grew hugely in confidence as the game became edgy, with Gattuso living up to his combative image and being booked. He will now miss the second leg and could face a Uefa charge for his behaviour.
Milan thought they had equalised late in stoppage time but Ibrahimovic's spectacular overhead strike was ruled out for a push.
At the Mestalla, Soldado put Valencia ahead in the 17th minute but Raul equalised for Schalke midway through the second half, turning sharply to score with a low shot from 10 yards.
Schalke's Lukas Schmitz was sent off in stoppage time following his second yellow card.
Arsenal host Barcelona and Roma entertain Shakhtar Donetsk on Wednesday with the other four first-leg ties to be played next week.