After making his debut against Skonto Riga in a UEFA Champions League qualifier, Cudicini ended his first season at Chelsea with just 3 appearances in all competitions. He was however on the bench as Chelsea won the 2000 FA Cup Final. The following season, he started to appear more regularly and shared the starting spot with Ed de Goey (Cudicini started 23 league games, De Goey 15). Despite a brief challenge from Mark Bosnich in the 2001–02 season, he retained his first team place with a string of excellent performances.