Coppa Italia holders Napoli only eliminated 10-man Udinese in a penalty shoot-out after a thrilling 2-2 draw.
The winners of this straight knockout round go on to face Inter in the quarter-final on February 4.
The holders began the defence of their trophy, giving Manolo Gabbiadini his first start, while Simone Scuffet was given a rare chance in goal for the Friulani. Native Neapolitan Antonio Di Natale was on the bench, but Giampiero Pinzi, Alexandre Geijo, Maurizio Domizzi, Emmanuel Badu, Molla Wague and Lucas Evangelista were unavailable.
After just two minutes Gabriel Silva had hauled down Duvan Zapata with an arm round his neck for an inevitable penalty. However, Dries Mertens blasted the penalty on to the crossbar and this early gift to Napoli went begging.
Udinese threatened to break the deadlock too, Cyril Thereau’s angled drive just wide of the far post with Nabil Jaadi sliding in unable to get the tap-in. It was a fast and furious start to the Round of 16 tie, as Gabbiadini’s header was punched out from under the bar by Scuffet.
Udinese also had penalty appeals for a Walter Gargano handling offence, but it ricocheted off his head first and therefore under current rules cannot be considered voluntary.
Napoli rattled the woodwork for the second time after 35 minutes, as Gargano’s strike was deflected off Melker Hallberg to loop over Scuffet, bounce off the inside of the far post and back out.
It was raining heavily in Naples and there was an amusing moment on the touchline when Giandomenico Mesto’s sliding tackle accidentally felled Coach Andrea Stramaccioni. As the Udinese boss tried to help Mesto back to his feet, he slipped and fell over again.
Straight after the restart Bruno Fernandes forced Mariano Andujar to parry his snapshot, while Scuffet did the same on Marek Hamsik from close range. Andujar had to rush outside his box to stop Thereau finishing a dangerous counter-attack, but it was only a warning Napoli did not heed.
Udinese struck with a classic counter, as 18-year-old Jaadi sprinted from his own half and intelligently rolled across for Thereau when it was two against one.
Duvan Zapata earned another penalty after his shirt was lightly tugged by Thomas Heurtaux in a fairly soft decision. Mertens had missed the first one, so Jorginho stepped up this time and coolly sent Scuffet the wrong way to equalise.
The game turned on its head, as moments later Silvan Widmer received a second yellow card for blocking the path of Mertens. Danilo risked an own goal, turning just wide, but Andujar was at full stretch to deny Bruno Fernandes a shock winner.
Jonathan de Guzman’s strike was deflected off target by teammate Ivan Strinic’s face, while Heurtaux nodded a free kick over in stoppages.
Napoli failed to break down 10-man Udinese and the holders were forced into extra time. Straight away the minnows had a fantastic chance to restore their lead, as Rodrigo Aguirre battled past Miguel Angel Britos and a ricochet was going in before Mesto’s desperate goal-line clearance. Then Andujar flew to palm a Panagiotis Kone strike round the post.
Just as the crowd was getting frustrated at this performance, Hamsik unleashed an absolute blockbuster from the edge of the box into the far top corner that gave Scuffet no chance.
Udinese would not give in and Kone equalised with another fantastic goal, smacking a fierce shot on the volley that he kept remarkably low. The Greek midfielder has history at the San Paolo, scoring a legendary scissor-kick volley for Bologna’s 3-2 victory here in 2013.
Kone threatened another when pouncing on a Britos error, forcing Andujar into a save at full stretch, and Mertens turned a free header over, but the teams could only be divided by a penalty shoot-out.
It was a 100 per cent record until Allan, who saw his spot-kick beaten away by Andujar’s trailing hand. Gonzalo Higuain had the last penalty and converted to send Napoli through to the quarter-finals against Inter. Having beaten Juventus on penalties in the Super Cup last month, the Partenopei were successful again.
Napoli 2-2 Udinese aet
Scorers: Thereau 58 (U), Jorginho pen 65 (N), Hamsik 99 (N), Kone 104 (U)
Penalties: Bruno Fernandes (goal, U), De Guzman (goal, N), Guilherme (goal, U), Jorginho (goal, N), Kone (goal, U), Mesto (goal, N), Danilo (goal, U), Hamsik (goal, N), Allan (saved, U), Higuain (goal, N)
Napoli: Andujar; Mesto, Henrique, Britos, Strinic; Gargano (De Guzman 71), Jorginho; Gabbiadini (Callejon 83), Hamsik, Mertens; Duvan Zapata (Higuain 110)
Udinese: Scuffet; Widmer, Heurtaux, Danilo, Pasquale; Jaadi (Kone 72), Allan, Hallberg (Guilherme 75), Gabriel Silva; Bruno Fernandes; Thereau (Aguirre 72)
Missed penalty: Mertens 3 (N)
Sent off: Widmer 68 (U)