AC Milan's Kevin-Prince Boateng (R) challenges Tottenham Hotspur's Luka Modric during their Champions League soccer match against at White Hart Lane in London March 9, 2011. [Photo/Agencies]

LONDON - AC Milan failed to reach the Champions League quarterfinals for the fourth successive season Wednesday, with Tottenham advancing by holding the seven-time winners to a 0-0 draw and protecting a 1-0 first-leg advantage.

While Milan was sharper and more dangerous than at home, the Serie A leaders couldn't find a way past Tottenham, which is playing in the European Cup for the first time since 1962.

"It's a huge night for us," said Tottenham striker Peter Crouch, who scored the only goal at the San Siro. "We defended magnificently _ we had to dig in and defend from the front and I think we deserved it over the two legs."

Milan has now been eliminated by a Premier League side in the last-16 phase in three of the last four seasons since lifting the trophy in 2007.

"This year something should have changed because I think we have played some good football apart from the first half of the first leg," Milan coach Massimo Allegri said through a translator. "I feel bitter, I have regrets for myself, the players and the club ... over the course of the two games I think we deserved a little more."

The loss leaves holder Inter Milan, which Tottenham beat in the group stage, as Italy's last hope of reaching the final in north London at Wembley Stadium in May.

The first leg ended in a touchline fracas sparked by the hosts _ particularly Gennaro Gattuso, who was suspended for the return leg. The tempers were a lot calmer at White Hart Lane, but there was far more intensity from Milan, which was more dynamic and attack-minded in the first half.

While Tottenham goalkeeper Heurelho Gomes pushed a free kick from Zlatan Ibrahimovic wide, the Brazilian goalkeeper didn't look so assured in the 25th minute.

After racing off his line and mistiming his dive, Gomes was rounded by Pato, who crossed to Robinho. The resulting shot span off Benoit Assou-Ekotto and was only hooked off the line by William Gallas.

"It was hard work," Tottenham manager Harry Redknapp said. "You could see that tonight, they played (Clarence) Seedorf and people like that. It was difficult to get near Pato ... we got outnumbered in the middle of the park. They had extra men in there."

Tottenham struggled to find the space to provide any threat. Rafael van der Vaart shot wide after two minutes, sent a free kick over on the half-hour and fired a low shot at Christian Abbiati _ the first on target from the home side.

"We found it difficult to get the ball for long spells because they narrowed up the field with a diamond and we want to play with width," Redknapp said. "Sandro I thought was immense tonight for us in midfield ... he is strong, aggressive and got the ability to work for 90 minutes."

But the speedy play that has been the hallmark of Tottenham's debut campaign in the Champions League was more evident at the start of the second half.

From the restart, however, Spurs squandered a chance when Aaron Lennon crossed into the penalty area and Crouch headed across the face of goal rather than directing it at the net.

There was another letup for Spurs in the 67th when Gomes blocked Robinho's close-range effort and the loose ball was eventually scrambled clear.

Allegri refused to blame Milan's exit on his misfiring strikers.

"I felt we played pretty well up front," he said. "Ibrahimovic had a few attempts on goals and it would be wrong to just look for mistakes and criticize the performance ... he has showed good movement, he put his teammates into play and he is a great player."

The team now goes back to Italy to focus on protecting its five-point lead over Inter Milan in the league.

"The performance the guys put in today is very encouraging for us with the team top of the league at the moment and we intend staying there," Allegri said.

Progressing in the Champions League is vital for Spurs since they are fifth in the Premier League and three points behind Chelsea in the last qualifying spot for Europe's top competition.

Chelsea and Manchester United will play their last-16 second-legs next week, while Tottenham's north London rival Arsenal was beaten by Barcelona on Tuesday.

"They're the team you don't want to play at the moment," Redknapp said about the Spanish champions.