#1 Claudio Ranieri
The man who beat the 5000-1 odds and took Leicester City on a fairytale campaign in the 2015-16 season has to be in this list.
Unlike, other managers in this list he didn't start his professional managerial career in the Serie B, but in the Serie C, with Cagliari, who are Serie A regulars now. Though he did manage S.S.D. Puteolana 1902, for a year, it was his stint with Cagliari that got his career started.
After spells in Spain, he was appointed Chelsea manager in 2000. It was his first taste of the English football.
Even after four seasons he failed to win any major silverware and was thus relieved of his duties in 2004. And it was after 11 years and stints in Spain, Italy, Greece that he finally returned to Premier League in 2015.
This season saw the Foxes winning the league title for the first time in their history, also saw Ranieri winning The Best FIFA Men's coach award, Premier League Manager of the season award for the 2015-16 season.
Though he was fired midway through the next season, he is one the best Italian managers to have won the Premier League, that too with the underdogs Leicester City.