LONDON // Tottenham Hotspur pulled off a deserved 1-0 win at AC Milan and Raul made a scoring return to Spain to earn Schalke 04 a 1-1 draw at Valencia in Champions League last-16 first-leg matches on Tuesday.
Spurs, making their debut in the competition this season, outplayed the seven-times European champions in a bad-tempered game and England striker Peter Crouch struck the winner 10 minutes from time with a fine breakaway goal.
Tempers flared after the final whistle and Milan midfielder Gennaro Gattuso was involved in an angry altercation with Tottenham assistant coach Joe Jordan.
"It's a great night for the fans and a great night for Tottenham," Spurs manager Harry Redknapp said. "They lost their heads at the end there, they were rattled for sure, and I guess that's a good sign."
Gattuso apologised for his behaviour. "I lost control," he told reporters. "There is no excuse for what I have done. I take my responsibilities for that. I was nervous. I was wrong to do what I have done."
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 Serie A leaders 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 Mario Yepes.
Tottenham looked pleased to be heading for a draw before England winger Aaron Lennon burst into the Milan half and laid the ball off perfectly for the unmarked Crouch to score with a clinical low shot.
At the Mestalla, Roberto Soldado put Valencia ahead in the 17th minute but Raul equalised for Schalke midway through the second half with a trademark finish, turning sharply to extend his record Champions League goal tally to 69.
"He showed the class he has always had. He exploited his talents, not only for the goal but all the work he put in during the match," Schalke coach Felix Magath said.
Schalke defender Lukas Schmitz was sent off in stoppage time following his second yellow card.