Italiano set to challenge in fifth cup final in last four years

Vincenzo Italiano is fast becoming one of Italy’s most under-rated coaches, as when Bologna face Napoli on Monday, it’ll be his fifth cup final in the last four years.

The Rossoblu came back from an early Marcus Thuram goal to hold Inter 1-1 with Riccardo Orsolini’s spot-kick, then were victorious in the penalty shoot-out.

That means they will play against Napoli on Monday evening in the Supercoppa Italiana Final, the first ever edition in which Bologna have competed.

They qualified after winning the Coppa Italia Final against AC Milan last season, their first victory in 51 years.

Italiano is becoming a cup specialist

RIYADH, SAUDI ARABIA – DECEMBER 19: Vincenzo Italiano, Head Coach of Bologna FC 1909, looks on prior to the Supercoppa Italiana semifinal match between Bologna FC 1909 and FC Internazionale at King Saud University Stadium on December 19, 2025 in Riyadh, Saudi Arabia. (Photo by Yasser Bakhsh/Getty Images)

Italiano has made a real name for himself as a cup competition coach, because this is going to be his fifth final in just four years.

Before the two for Bologna, he took Fiorentina to back-to-back editions of the Conference League Final, plus a Coppa Italia Final.

Although he didn’t win any of those in charge of the Viola, they were still far more than anyone expected, especially in the light of their current struggles.

Italian head coach Vincenzo Italiano (C), now at Bologna, shouts instructions to his players from the touchline during the UEFA Europa Conference League final football match between Olympiakos and Fiorentina at the AEK Arena in Athens on May 29, 2024. (Photo by Aris MESSINIS / AFP) (Photo by ARIS MESSINIS/AFP via Getty Images)

Italiano, who celebrated his 48^th birthday earlier this month, lost the 2023 Conference League Final to West Ham United, and the 2024 edition to Olympiacos in extra time.

His Fiorentina also lost the Coppa Italia Final 2-1 to Inter in May 2023.