9) Afonso Alves (Heerenveen – Middlesbrough £12.5m – 2008)
The Brazilian’s transfer to Middlesbrough is one of the most notorious in Premier League history. His form in Holland was sensational, having bagged 37 goals in the 2006/07 season for Heerenveen, and he continued that form into 2007/08, scoring SEVEN in one match against Heracles. That led to Boro shelling out a sizeable transfer fee on him.
Alves did have a good start after arriving at the Riverside Stadium, scoring six in 11 appearances over the second half of the 2007/08 season (including a hat-trick on the final day against City). However, the following campaign saw him score just six in total, leading to him being shipped out Al-Sadd after failing to prevent the Teessiders from being relegated.
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