Milan recovered from a disastrous first half performance, but could only manage a 0-0 Champions League draw with Anderlecht amid jeers from the fans.
The Rossoneri began their European campaign with tension sky high after losing both their Serie A home games against Sampdoria and Atalanta. With Alexandre Pato and Robinho injured, Coach Max Allegri opted for a trident with Kevin-Prince Boateng and Urby Emanuelson supporting Giampaolo Pazzini. The Belgians were back in the group phase of the Champions League after a six-year absence, but missed full-back Denis Odoi.
It was a nervy start, as Nigel De Jong gave the ball away cheaply, then Marcin Wasilewski had his shot blocked by a crowd of bodies from a corner.
Anderlecht started to take control and on 12 minutes Christian Abbiati got down to palm a long-range Sacha Kljestan shot round the near post.
Luca Antonini’s glancing header from a corner was well wide and Milan created a great chance when Mattia De Sciglio’s effort was deflected into the path of Mathieu Flamini, hist finish charged down from six yards.
Anderlecht continued to swarm around the Rossoneri’s final third, though, and Guillame Gillet skipped past his marker at the by-line to test Abbiati at the base of the near stick.
Boateng chested down an Emanuelson cross and his half-volley whistled inches wide of the upright. A long ball found Emanuelson and it dropped over his shoulder for a volley that was well held by goalkeeper Silvio Proto.
Dieudonne Mbokani’s overhead kick was off target, prompting some jeers from the increasingly frustrated San Siro crowd. A promising counter-attack came to nothing when Emanuelson’s pass was well behind both Pazzini and Boateng.
Milan were playing with a tangible sense of panic and in the first half Anderlecht had 53 per cent of the possession.
After the restart Antonio Nocerino was incorrectly flagged offside, but had nodded off target anyway. Lucas Biglia burst down the right past Luca Antonini and Daniele Bonera, firing over the bar from a dangerous position.
Pazzini did well to hold off defenders and set up Emanuelson, but the angled drive was scuffed. Stephan El Shaarawy replaced Boateng, who was jeered and took out his frustration on the bench, left almost in tears.
The ‘Little Pharaoh’ made an immediate impact, as he got between defenders for a header into the ground on Emanuelson’s cross, forcing Proto into a parry from point-blank range.
Pazzini just failed to get on the end of De Sciglio’s low cross moments later as he came sliding in from six yards.
Milan seemed to find an extra gear and considerably more confidence, but Emanuelson blasted over when he perhaps should’ve left the through ball for Nocerino. El Shaarawy turned an audacious volley well over.
The second substitution was forced, as Mario Yepes replaced the injured Bonera after a knock to the foot, while Kevin Constant came on for the exhausted Emanuelson. Kljestan was then booked for a very high tackle on Flamini and the Frenchman followed him into the list of yellows.
It’s a disappointing start for the Rossoneri, so Malaga now lead Group C after their 3-0 victory over Zenit.
Milan 0-0 Anderlecht
Milan: Abbiati; De Sciglio, Bonera (Yepes 74), Mexes, Antonini; Flamini, De Jong, Nocerino; Boateng (El Shaarawy 60), Emanuelson (Constant 78); Pazzini
Anderlecht: Proto; Gillet (Juhasz 78), Wasilewski, Nuytinck, Deschacht; Bruno, Biglia, Kouyate (Praet 78), Kljestan; Kanu (Yakovenko 89); Mbokani
Ref: Collum (SCO)