3. Raymond de Waard
Another Dutchman signed by Bryan Hamilton, that failed to hit the ground running. Raymond de Waard was signed towards the end of the 1999-00 season, with the club paying £225,000 for his services.
He was famous for having electric pace but looked like he always at least ten seconds behind play. De Waard was a disappointment for the Canaries, which was not helped by injuries and he was released by Hamilton’s successor Nigel Worthington in March 2001.
2. Ricky van Wolfswinkel
Yes, that’s right, another Dutchman. Wolfswinkel had scored 20 goals in 40 appearances for Portuguese giants Sporting before Norwich secured his services for £8.5million in 2013. He scored on his debut but managed no further goals in his next 23 league games for the club.
Norwich were relegated from the Premier League that season. The striker spent the majority of the next two seasons on-loan in France and Spain. In July 2016, he re-joined former club Vitesse, and his painful tenure at Carrow Road was over.
1. Michael Theoklitos
Theoklitos only played one game for Norwich during his time at the club, and it was a game that remains one of the club’s darkest hours to this day. He would debut in the opening game of the 2009/10 League One season. Theoklitos conceded five goals before half time itself. Norwich were thrashed 7-1 by East Anglian rivals Colchester, and Theoklitos would never play for the club again.