Milan fumbled a 2-0 lead, but thanked an own goal, Stephan El Shaarawy’s splendid solo effort and Christian Abbiati’s heroics for a 3-2 win over Zenit in Russia. It's a particularly remarkable result considering Zenit's last European home defeat was in 2008.
Luciano Spalletti and Domenico Criscito welcomed the Rossoneri to St Petersburg for the second Champions League game of the group, which already felt decisive. Zenit were beaten 3-0 in the opener by Malaga, while Milan were held on home turf by Anderlecht.
Bojan Krkic was given a rare start with Stephan El Shaarawy and Kevin-Prince Boateng, while Urby Emanuelson was picked ahead of Antonio Nocerino. Bruno Alves and Igor Denisov were dropped due to poor form, while Axel Witsel – a former Milan transfer target – made his first start since joining from Benfica. Both Criscito and Nicolas Lombaerts wore face masks after picking up injuries at the weekend.
Emanuelson tested Vyacheslav Malafeev in the opening five minutes, but Bojan was offside on the rebound as Milan went looking for their first Champions League away win since November 2010.
The Italians did take the lead with a stroke of luck, as Emanuelson’s free kick from 25 metres took a huge deflection off the defensive wall to leave Malafeev wrong-footed and loop in at the far post.
Emanuelson almost bagged a second just a minute later, as he was at full stretch to turn a Luca Antonini cross on to the side-netting at the back stick.
There was no luck in El Shaarawy’s goal, though, as the Little Pharaoh single-handedly dribbled through the entire Zenit defence and fired past the goalkeeper from 12 yards. It was a wonderful individual effort from the 19-year-old, who started his run in midfield and rode several tackles. Not only was it his fifth goal in four games, but he also became the youngest ever Champions League scorer for Milan aged 19 years and 342 days.
Bojan ran into the box and fell over a risky challenge, but the referee waved play on. Zenit’s first chance came on 23 minutes with Aleksandr Kerzhakov hitting the side-netting, but then a corner led to Roman Shirokov’s glancing header and a splendid Christian Abbiati save from close range.
Vladimir Bystrov blasted well over from distance, as Zenit started to take more possession, and Abbiati held a dangerous cross deflected off Antonini into the path of Shirokov. Malafeev had to scramble back to stop a Boateng cross-shot from going over the line.
Moments later, Abbiati flew to palm a sudden Hulk screamer out from under the bar. From the corner, he blocked Shirokov’s header right on the goalline. Abbiati again got down to beat away a Tomas Hubocan header from a free kick.
El Shaarawy got back to defend and nudged over Viktor Fayzulin on the very edge of the box after a gap had opened up in the Milan line. From that free kick, Hulk’s ferocious low strike was brilliantly taken off the line with one strong Abbiati hand.
However, the goalkeeper was finally beaten in first half stoppages when Hulk ran on to a Shirokov through ball down the left side of the box and smashed the angled drive across Abbiati.
Zenit came out stronger for the second half and equalised almost immediately. As shown many times, Milan have problems from set plays and a Hulk corner was whipped straight to Shirokov for a cushioned header at the back post fairly undisturbed. He had got away from Riccardo Montolivo.
Max Allegri introduced Giampaolo Pazzini for the ineffective Bojan and Boateng’s free header whistled wide from eight yards, as he was a little in front of Abate’s cross.
Play was halted at 58 minutes because a hole was spotted in Abbiati’s net. Curiously, it was Zenit midfielder Bystrov who decided to fix it himself with a few well-placed knots.
The game was more balanced after a period of Zenit pressure and Milan restored their lead. Montolivo’s taut cross from the right was aimed towards Pazzini as he came sliding in at the near post, but appeared to go in off Zenit defender Tomas Hubocan instead from a couple of yards.
Abbiati needed a sensational save to keep his men in front, as a corner came out to Aleksandr Anyukov on the edge of the box and the half-volley was arrowing its way in low at the near post, but the goalkeeper got down quickly to palm it round the upright with one hand. The veteran celebrated as if he’d just scored and it was a save worthy every bit as much as a goal.
Mario Yepes came off the bench and within minutes got booked for an incredibly high flying tackle.
Zenit 2-3 Milan
Scorers: Emanuelson 13 (M), El Shaarawy 16 (M), Hulk 45 (Z), Shirokov 49 (Z), Hubocan og 76 (M)
Zenit: Malafeev; Anyukov, Hubocan, Lombaerts (Bukharov 89), Criscito; Fayzulin (Kanunnikov 79), Witsel, Shirokov; Bystrov (Zyryanov 72), Kerzhakov, Hulk
Milan: Abbiati; Abate, Bonera, Zapata, Antonini; De Jong, Montolivo; Emanuelson (Nocerino 64), Boateng (Yepes 80), El Shaarawy; Bojan (Pazzini 52)
Ref: Brych (GER)
Think you know your Italian football? Share your knowledge, tips and comments to win cash prizes in OLBG's World Cup tipster competition  - £10,000 to be won!