Kick-off: 19.12.23 at 22:00.

The Parthenopeans start their journey in the tournament. According to the rules, teams from the top eight of the previous Serie A season enter the competition only in the upcoming stage. The Canaries defeated Torino in the Round of 32 at the Olimpico Turin, opening the scoring as early as the fifth minute (2-1, overtime). Nine out of twenty shots from Chouchane missed the target. The Yellow and Blues created fewer dangerous attacks (35-77), committed fouls in only eight episodes, and goalkeeper Cherubini made ten saves.

Watch the Napoli vs. Frosinone match online; the opponents crossed paths in the Round of 64 in the 2006/07 season when both teams were in Serie B. Napoli won that encounter 3-1. Since 2013, the Azure-Whites have been eliminated in this round only twice. These instances were in the two previous editions, resulting in defeats to Fiorentina (2-5, overtime) and Cremonese (2-2, 4-5 on penalties).

Since the early 2000s, the current Serie A champion has halted their trophy quest seven times at the nearest stage. In the 2005/06 tournament, Napoli, playing in the third division, lost to Roma (0-3, 1-2). In the next two competitions, they were defeated by Parma (1-0, 1-3) and Lazio (1-2, 1-1). In the 2009/10 season, Napoli couldn't pass Juventus, 0-3, and three years later, they lost to Bologna, 1-2. Watch the Napoli vs. Frosinone game online.

Frosinone started in the Round of 32, defeating Pisa from Serie B at home with an own goal in the seventh minute. The Lions will make their debut in the upcoming stage for the first time in history. The Little Donkeys were content with lower divisions for a long time, so they only made their debut in the Italian Cup eighteen years ago.

Three times, the Canaries were halted in the Round of 16, setting a record for the team. These were in the 2009/10 (Chievo, 0-2), 2013/14 (Avellino, 1-2), and 2019/20 (Parma, 1-2) editions. In the previous tournament, Chouchane was eliminated in the Round of 32, letting Monza pass with a score of 2-3. Watch the Napoli vs. Frosinone match online.