Things didn't get off to a great start for Napoli. They won a penalty almost right off the bat when Gabriel Silva spun Duvan Zapata to the ground in the second minute, but Dries Mertens' try at the spot kick clanked off the bar and out to safety. That was, unfortunately, a herald of the way the day would go for Napoli.
Time and time and time again, Napoli got forward, but their every effort was blocked or deflected or fizzled to nothing because no one made a supporting run. Twice in the first half, Marek Hamsik put in a note-perfect through ball, but the runs he was expecting from his fellow attackers to capitalize on it didn't materialize. The second half was much the same, highlighted by a perfectly-dropped cross to the far post by Ivan Strinic, but the Croatian was holding his head before the ball even arced down because Manolo Gabbiadini simply didn't make the run that was expected.
Shortly after that, after yet another blocked shot, Napoli got ripped open on the counter, with Cyril Thereau getting on the end of a two-on-one attack that left Henrique Buss crossed up and Mariano Andujar going the wrong way before the shot was even taken to go up 1-0 just before the hour mark.
It wasn't long before Napoli equalized, though it wasn't without controversy. Zapata again went down in the box, this time with Thomas Hertaux adjudged to have brought down the big Colombian. Replays certainly showed contact between the two, though arguably not enough to call a penalty. The referee was at a bit of an awkward angle, though, and may have felt a need for a make-up call after not awarding Zapata a second penalty late in the first half -- he was hit hard by Danilo, but fought through the foul and ultimately lost the ball -- and awarded Napoli their second spot-kick of the match. Jorginho stepped up this time, and unlike Mertens he had no issues converting his shot.
Just a few minutes later, Udinese were dealt another blow: wing back Silvan Widmer was dismissed after being shown his second yellow card of the day when he hacked down Mertens at the edge of the box. Referee Daniele Orsato was very willing to hand out yellow cards during this match, with that being the sixth yellow card he'd shown an Udinese player on the day, and ultimately handed out nine total cards in the match.
Napoli never really seemed to take full advantage of being a man up, though, as they never blitzed Udinese's depleted defense or took full control of the ball. They certainly made efforts at attacking, but the same problems kept plaguing them: blocks, deflections, and lack of support.
And so things carried on in to extra time, where Udinese suddenly seemed to be on the front foot, getting the better of the early chances and keeping Napoli off balance despite being a man down. Hamsik didn't care, though, unleashing a simply fantastic goal in the 99th minute that left everyone's jaws on the floor. That advantage didn't last long, though, as Panagiotis Kone was left unmarked at the top of the box, receiving a cross and volleying it home with aplomb. Back and forth the match went for the rest of extra time, with Udinese getting the better of the challenges and Napoli mostly failing to get the ball to a dangerman, even once Gonzalo Higuain was (finally) introduced to the match well in to the second extra time period.
Penalties beckoned, and each side made their first four tries, including a soft hit from Kone that Andujar somehow managed to get a full hand on but let in anyways. Andujar more than made up for it on Udinese's next try, though, getting both hands on Allan's penalty and sending it booming away, setting up Higuain to drill the winner.
Napoli move on to the quarter finals, drawn with Inter Milan after they beat Sampdoria 2-0 on Wednesday. Hopefully Napoli play that match a fair sight better than they did today, or else their Coppa Italia title defense will end far earlier than it should.
Napoli: Andujar; Mesto, Henrique, Britos, Strinic; Gargano (de Guzman 71'), Jorginho; Gabbiadini (Callejon 84'), Hamsik, Mertens; Zapata (Higuain 111')
Goals: Jorginho 65' (pen.), Hamsik 99'
Udinese: Scuffet; Widmer (red card 68'), Heurtaux, Danilo, Pasquale; Jaadi (Kone 72'), Allan, Hallberg (Guilherme 76'), Silva; Bruno ; Thereau (Aguirre 72')
Goals: Thereau 58', Kone 104'