Cudicini started his professional career at Serie A side AC Milan in 1992, but struggled to break into the first team and was loaned to Como before moving to Prato and then Lazio in 1996.He remained first choice under Claudio Ranieri, but lost his starting spot to new signing Petr Čech in 2004 under new manager Jose Mourinho.Cudicini left Chelsea in January 2009, having made 141 league appearances for the club, and joined local rivals Tottenham Hotspur.[citation needed] After making his debut against Skonto Riga in a UEFA Champions League qualifier, Cudicini ended his first season at Chelsea with just three appearances in all competitions.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.On 14 October 2006, in a league game against Reading, he was knocked unconscious and had to be stretchered off the pitch while wearing an oxygen mask after coming on as a substitute for first-choice goalkeeper Čech.He played against Leicester City in a 4–3 win at Stamford Bridge in the next round before making his first appearance of the season in the Champions League, coming on as a substitute against Schalke 04.Cudicini then featured in the next five games due to Čech's injury, conceding just one goal in the process, against Everton at Stamford Bridge in a 1–1 draw.He featured in both legs against Turkish club Fenerbahçe as Chelsea progressed 3–2 on aggregate; unfortunately; he limped off with an injury that effectively ended his season.Cudicini made his first competitive appearance in nearly six months for Tottenham when he came on as a substitute for the injured Heurelho Gomes in a 5–1 victory over Hull City on 19 August 2009.On 25 August 2010, Cudicini saw his first official action for the club in nearly a year as a half-time replacement for the injured Gomes in the second leg of Tottenham's UEFA Champions League play-off round tie against Young Boys of Switzerland.[17] Three days later, he started against Wigan Athletic in the Premier League at White Hart Lane but was criticised for conceding the Latics' winning goal scored by Hugo Rodallega.Despite putting in some consistently good performances for Spurs, he was again benched in favour of Gomes for the Champions League group stage match against Twente on 29 September.He was an eighth-minute replacement for Luka Modrić after Gomes' sending-off against Inter Milan on 20 October, but was powerless to stop the defending Champions League winners from scoring three times in a 4–3 loss at the San Siro.He was not eligible for England because FIFA Statutes stipulate that the player needs to have held a British passport at the time when he represented Italy at the U16 European Championship, and would have required five years of education in Britain before turning 18.[40] In August 2019, Cudicini had been appointed technical coach for the players on loan from other clubs, following Eddie Newton's move to Frank Lampard's backroom staff.