AC Milan limps to goalless UCL draw
Milan was hoping for a positive result after a dismal start to the season which has seen it lose its first two home games for the first time in 82 years.
However, an error-strewn performance saw Milan again fail to score at home, for the third time this campaign, and Massimiliano Allegri's team were roundly jeered off the pitch both at halftime and full time.
Anderlecht looked much the better side and only some poor finishing ensured it failed to win in Italy for the first time in its history.
Philippe Mexes was back from injury and made his first appearance of the season, but he clearly lacked match fitness and added to Milan's errors.
Milan went on to win the Champions League both times it has previously faced Anderlecht in the group stages, but it will have to improve dramatically if history is to repeat itself.
Both of Milan's Brazil forwards, Alexandre Pato and Robinho, are working their way back from leg muscle injuries and Allegri will want the duo back as soon as possible as his attack is clearly struggling after the sale of Zlatan Ibrahimovic.
Milan was looking to get off to a good start to get its supporters back on side, with less than 28,000 spectators at the 80,000-capacity San Siro reflecting the team's dismal performances of late.
Nigel De Jong was making his Champions League debut for the club but a woeful back pass almost led to an Anderlecht goal in the opening two minutes. Daniele Bonera was forced to concede a free kick and seconds later Kanu headed narrowly over.
The errors continued to pile up and Anderlecht could have taken the lead when a one-two between Dieudonne Mbokani and Sacha Kljestan saw the latter unleash a curling shot which Milan goalkeeper Christian Abbiati did well to tip round the post at full stretch.
Milan slowly began to get in the game and had its first opportunity in the 15th minute when Kevin-Prince Boateng got a heel to a good cross from Mattia De Sciglio, but his effort was deflected narrowly wide.
Giampaolo Pazzini, who had scored all three of Milan's goals this season, started to make his presence fell but a cross from Luca Antonini was just too high for the former Inter Milan striker.
Moments later Milan had one of its best chances of the game as the ball ping-ponged around the area before falling to Pazzini who picked out an unmarked Mathieu Flamini, but his snapshot was well saved by Anderlecht goalkeeper Silvio Proto.
Anderlecht almost went in front in the 27th minute when Guillaume Gillet did well to keep the ball in play and force his way into the area. His cross-shot almost crept in at the near post but Abbiati reacted well.
Milan should have taken the lead shortly after the half hour when Urby Emanuelson picked out an unmarked Boateng, whose effort was comfortably saved by Proto.
Antonio Nocerino then put a long ball over the defense for the onrushing Emanuelson but his volley was well saved by Proto.
Anderlecht could have taken a halftime lead when Massimo Bruno saw his effort cleared by Mexes but the ball came to Mbokani who tried an acrobatic effort which sailed well wide of the right upright.
The Congolese striker injured himself in the process and had to receive treatment.
Milan was slightly improved after the break and could have taken the lead two minutes after the restart when Nocerino's header scraped the top of the crossbar, although it was dubiously flagged offside.
However, Anderlecht went closest when Mbokani released Lucas Biglia who found himself one-on-one with Abbiati but could not find the target.
Stephen El Shaarawy came on for Boateng on the hour and had Milan's best chance of the night shortly after, as he powerfully headed Emanuelson's cross towards goal, only to be denied by a brilliant stop by Proto on the line.
El Shaarawy turned provider for Emanuelson minutes later but the Dutchman blazed over the crossbar from a good position.
Anderlecht could have scored in the dying minutes but Mario Yepes did well to clear the ball away from the onrushing Mbokani following a poor back pass from Antonini.