Son of former Roma and AC Milan goalkeeper Fabio Cudicini, Italian youth international stopper Carlo spent the early stages of his career in his homeland before coming to the UK with Chelsea in 1999 in a loan deal from Castel Di Sangro. He made his Blues debut as a substitute for Ed De Goey in the second leg of a UEFA Champions League qualifier at Latvian side Skonto in August that year before making his Premier League bow from the start in a 4-0 home win over Derby County at the end of the 1999-2000 season.
On the bench as Chelsea won the FA Cup Final in 2000, he was promptly snapped up on a permanent deal and proved to be a good servant to the Stamford Bridge club over the next nine years.