Milan were punished for a docile second half performance and taken into extra time by Novara before eventually winning their Coppa Italia clash.
Both sides went into the Last 16 clash in need of a good performance after respective disappointing League defeats at the weekend.
Massimiliano Allegri rang the changes after his team’s derby defeat, notably bringing in the likes of Philippe Mexes, Massimo Ambrosini, Stephan El Shaarawy and Filippo Inzaghi for starts. Alexander Merkel was also handed a first-team chance after his midweek loan return from Genoa.
Similarly, Attilio Tesser made seven changes to his line-up after their Week 18 defeat to Cesena.
Milan carved open the first opportunity of the tie after seven minutes. El Shaarawy’s quick release of the ball in the penalty area found Inzaghi, but his clever turn was followed by a tame shot.
The Rossoneri dominated possession in the early stages and it was Inzaghi who again popped up for their next two chances.
Whilst Novara’s goalkeeper Alberto Fontana was quick off his line to prevent the veteran springing the offside trap, the striker guiltily missed a headed effort at the far post moments later.
Soon after that Simone Pesce tested Marco Amelia’s alertness with a stinging effort that forced a corner.
El Shaarawy demonstrated his potential with a well-taken strike, taking possession outside the area on the left to cut in an unleash an outward curling effort low and past Fontana.
Granoche almost equalised immediately, latching on with a toe-poke to try to finish a clever passing move through Milan’s defence, but the effort was straight at Amelia.
With 10 minutes of the first half remaining, El Shaarawy almost doubled his tally on the night after latching on to a long pass down field that caught Novara’s high line of defence out. However, his cut inside and high effort was tipped over by Fontana.
A quieter second half was peppered by roving runs through Novara’s defence by both El Shaarawy and Urby Emanuelson, but on each occasion to no distinct end product. Indeed, the second 45 was characterised by the home team’s comfort in possession matched with a wastefulness in the final third.
Emanuelson forced a routine save from Fontana midway through the period after neat work down the right from substitute Alexandre Pato.
At the other end, Michel Morganella’s dangerous cross forced an improvised and careful clearance behind by Mexes.
Some skill in the middle of the pitch by El Shaarawy, followed by a run down the pitch with the ball from Robinho lifted the atmosphere heading towards the closing stages, before Pato’s subsequent effort on goal thundered over the bar by some distance.
From nothing, Radovanovic equalised with two minutes to go when his low 30-yard free-kick found its way through the Milan wall and easily past a rooted Amelia.
In his side’s immediate attacking at the other end, Luca Antonini received a nasty blow to the head from Jeda’s boot after the Novara player’s acrobatic attempt to clear a cross on the edge of the penalty area. Pato shot wide from the resulting free-kick.
Radovanovic and Robinho picked up yellow cards for clashing after the Brazilian’s challenge on the midfielder. Milan returned to dominating possession in extra time having dropped off towards the end of the original 90. Ignazio Abate’s cross was met with a close-range half-volley from Pato for the team’s first clear-cut chance, but Fontana’s outstretched hand proved enough to keep the scores level.
Minutes later though, Pato did get the better of the ‘keeper, flicking it over his run off his line to then casually volley it into an empty net. Pato, who narrowly beat the offside trap, had been put through one-on-one from Robinho’s slide-rule pass.
Robinho then almost made it three, controlling a loose ball in the box, only to see his volley shave the outside of Fontana’s right post. Pato then almost got a second with an acrobatic bicycle kick just before the end of the first half of extra time, controlling an El Shaarawy cross before swivelling on the spot and lashing just wide.
Bonera did well to block a late, point-blank effort from Jeda that would have forced the tie into penalties. It came during the final few minutes when Milan were playing with 10 men. Having used all three substitutions, Pato’s withdrawal for what looked like a slight hamstring injury left the team a man down.
Milan 2-1 Novara (after extra time)
Scorers: El Shaarawy 24 (M), Radovanovic 88 (N), Pato 99 (M)
Milan: Amelia; Bonera, Nesta, Mexes, Antonini (Abate 91); Merkel, Ambrosini, Nocerino; Emanuelson (Robinho 82); Inzaghi (Pato 58), El Shaarawy
Novara: Fontana; Morganella, Dellafiore, Paci, Centurioni (Jeda 77), García; Marianini (Jensen 54), Radovanović, Pesce; Granoche, Morimoto (Rubino 63)