Monza vs. Brescia (Thursday, 5.30pm)
Still without a Serie A success this season, Monza aim to end their wait for a win on Thursday, when they host Brescia in the Coppa Italia.
While Alessandro Nesta's side are struggling in the top flight, their visitors are inside Serie B's top six and will hope to push for promotion over the months ahead.
We say: Monza 1-0 Brescia
It is set to be a close contest between two Lombardy clubs that have never lifted the Coppa Italia, but due to their greater individual quality, Monza should just scrape through to meet Bologna in the last 16.
Napoli vs. Palermo (Thursday, 8.00pm)
Flying high in Serie A, where they sit second after five rounds, Napoli will meet Palermo in the Coppa Italia second round on Thursday.
This year seeking a seventh cup win, the Azzurri welcome their Sicilian counterparts to Stadio Maradona fresh from a goalless draw with Juventus.
We say: Napoli 2-0 Palermo
Even Napoli's second string - if selected by Antonio Conte - has a strong look, since some summertime spending rejuvenated a slightly jaded squad.
Therefore, the hosts should see off Palermo and move one step closer to Conte's objective of winning some silverware in his first season.