Monzeglio had a highly successful career as a footballer, although he also later attracted controversy due to his close relationship with the Italian fascist dictator Benito Mussolini.

Along with Giuseppe Meazza and Giovanni Ferrari, he is one of only three Italian players to have won two World Cups.

[3] In his nineteen-year career as a football defender, which lasted from 1924 to 1943, he played for Casale, Bologna, and Roma.

[3][5][6] Despite his success and fame as a footballer, following the conclusion of the Second World War, however, Monzeglio had initially attracted controversy, due to his political views and close friendship with the Italian fascist dictator Benito Mussolini, as well as his role as Mussolini's personal coach.

[7][8] Monzeglio later became a coach, managing the Italian teams of A.S. Roma, Como, Pro Sesto, Napoli, Sampdoria, Juventus, and Lecco, as well as Chiasso, in Switzerland, between 1941 and 1973.