#2 Boudewijn Zenden
Zenden was signed by Claudio Ranieri in 2001 and played a pivotal role in Chelsea’s rise to prominence making 57 appearances in two seasons.
The winger was soon to be troubled by a lack of form and fitness and was loaned to Middlesbrough in the 2003/04 season. After an eye-catching spell at Middlesbrough, the Dutch midfielder was brought to Liverpool in 2005.
“Bolo” as he was called had made 46 appearances during his time at the club but suffered a string of knee injuries and missed out on the club’s FA Cup win against West Ham.
Zenden did manage to play in Liverpool’s 2007 Champions league final against AC Milan but only to see his club loss to the Italian side. After Zenden’s contract expired at Liverpool the player departed from Merseyside joining Marseille on a two-year deal in July 2007