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. He was voted Chelsea's Player of the Year for the 2001–02 season by fans, reflecting the value he added to a team struggling for consistency. In December 2001, he saved two penalties in a span of seven days from Sunderland's Kevin Phillips and Liverpool's Gary McAllister. Cudicini was recognised as the best goalkeeper in the Premier League in the 2002–2003 season, when he won the ITV Premiership Goalkeeper of the Season award. Cudicini also saved a penalty from Arsenal's Thierry Henry to help earn his side a replay in the FA Cup. After a bright start to the 2003–04 season, the old injury problems experienced in his Lazio days came back, leaving him unable to carry on his success from last season and unable to play for a large portion of the season. His value to the team was highlighted when Chelsea's replacement goalkeeper Marco Ambrosio failed to effectively fit into the first team, leading to Chelsea's exit from the Champions League at the semi final stage to Monaco. He further demonstrated his penalty saving prowess with a save from Manchester United's Ruud van Nistelrooy in a crucial Premier League tie. However, he later made a mistake in the same game and allowing the same player to equalise, but Chelsea nonetheless secured a 1–1 draw that was enough for automatic UEFA Champions League qualification. 2004–05 The 2004–05 season saw the arrival of new manager José Mourinho. Cudicini saw competition after the arrival of Petr Čech. Čech claimed that he would push Cudicini for a first team place and Cudicini was dropped to the substitute bench. As a result, he missed out on a Premier League winners' medal as he managed only three league appearances all season, all of which came after Chelsea had secured the trophy. He did, however, feature in most of Chelsea's FA Cup and League Cup games that season. Chelsea reached the 2005 Football League Cup Final, however