The home side had screams for a penalty after only 4 minutes when Bruno Alves went over the back of Giampaolo Pazzini close to goal, taking the Italian down in the process. However, the referee waved play on despite Milan's vehement protests over what appeared to be a fairly clear foul.
Hulk skied a header high over the bar from a Sergei Semak cross, whilst Urby Emanuelson's attempt from distance was blocked at the other end as each side probed for a weakness in the opposing defense.
The Dutchman again went for goal from outside the area soon after, but was thwarted once more by the well-positioned Nicolas Lombaerts. The resulting corner was swung in well at the far post, but was cleared away to end the danger.
Semak cut in from the right flank with a clever bit of skill to shoot in space from 18 yards, but fired just above Christian Abbiati's net to send the chance went begging.
Christian Zapata failed to hit the target with an acrobatic effort on 22 minutes, while Mathieu Flamini's right-footed drive from distance spiraled wide of the mark from the outside of the Frenchman's boot.
On 35 minutes, Zenit took the lead against the run of play. The ball came loose in the area as Zapata tangled with Hulk, and Portuguese international Danny reached it first to smash an angled drive past Abbiati at the far post.
Flamini tested Vyacheslav Malafeev from long range, but the Russian veteran was equal to the task in beating away the fierce dipping effort.
Pazzini flashed a header across the face of goal on the stroke of halftime from an Emanuelson cross as Milan went into the break down 1-0 despite having taken 6 more shots and claiming 61% of the possession in the first half.
After the restart, a well-worked counter saw Kevin-Prince Boateng find Pazzini with a low cross for the Italian to go for goal on the slide at close range, but a wonderful reaction save from Malafeev with his right foot kept the Russians in front.
On 59 minutes, Semak attempted to catch Abbiati napping from 30 yards on the counterattack, but the Milan keeper easily gripped the relatively central effort.
Massimiliano Allegri replaced Djamel Mesbah with Robinho, transitioning Milan to a system with three at the back, as the Rossoneri continued their quest to find an equalizer.
Boateng had an attempt on the half volley from distance, but couldn't keep his shot sown and blazed well over the bar.
Robinho played Bojan into the area for the Spaniard to get himself into a dangerous position, but the diminutive Barcelona youth product overcooked his touch and saw the ball cleared away.
Luciano Spalletti withdrew Hulk on 80 minutes for central defender Konstantin Zyryanov, whilst Allegri surprisingly brought on Stephan El Sharaawy for Mathieu Flamini regardless of the unimportance of the match to Milan's fortunes.
Robinho nearly drew level for the Diavolo with a curling effort from the left side of the box, but went just wide of the mark. Soon after, El Sharaawy also narrowly missed on the turn with his left foot.
17 year-old Milan youth Andrea Petagna was the final substitution of the match for the home side, whilst the visitors threw on Maksim Kanunnikov and Michael Lumb for the final minutes.
Zenit nearly bagged a second in extra time when a counterattack saw the Milan defense pulled apart by overlapping runs, but Abbiati saved Konstantin Zyryanov's snapshot from close range.
Stat of the Match: Milan had 19 total shots to Zenit's 6, but each team had an equal 3 shots on goal
Man of the Match: Danny, Zenit St. Petersburg (1 goal; 83% passing)
Highlights
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