Fiorentina saw off nine-man Napoli 5-2 in extra time on Thursday to reach the Italian Cup quarter-finals, while AC Milan also needed 30 added minutes to get past Genoa.
It is the eighth time in 10 seasons that Fiorentina have made the Cup quarters.
Dusan Vlahovic, who has been heavily linked with a move away from Florence, put the visitors ahead with his 19th goal of the season four minutes before half-time, as the game burst into life.
Napoli winger Dries Mertens levelled just three minutes later, before Fiorentina goalkeeper Bartlomiej Dragowski was sent off for a cynical block on Elif Elmas as the Macedonian looked to take advantage of a defensive mix-up.
But the 10 men restored their lead in the 58th minute as Italy left-back Cristiano Biraghi pounced on a rebound inside the box to score.
Napoli also had a man dismissed, as substitute Hirving Lozano was shown a straight red card after a VAR review.
The hosts’ tempers boiled over further in stoppage time, with another sub, Fabian Ruiz, given his marching orders for a second booking.
But just seconds later, Napoli’s Andrea Petagna slotted in a remarkable equaliser to force extra time.
Fiorentina made their man advantage count, though, as Lorenzo Venuti and Krzysztof Piatek netted either side of half-time in extra time.
Moroccan Youssef Maleh added a fifth as his side eased into a last-eight clash with Atalanta, who beat Venezia 2-0 on Wednesday.
Milan, who sit second in Serie A behind city rivals Inter, came from behind to beat Genoa 3-1 after extra time at the San Siro.
Genoa led for almost an hour after Leo Ostigard’s 17th-minute opener, but Olivier Giroud struck 16 minutes from time to draw the home side level.
Rafael Leao, with a mishit cross which flew straight in, and Alexis Saelemaekers both found the net in the extra half-hour as Stefano Pioli’s Milan set up a quarter-final against either Lazio or Udinese.
The other five last-16 ties will be played next week.