2. Afonso Alves - Heerenveen to Middlesbrough, 2008
Afonso Alves' biggest moment in his football career probably came when he scored a last-minute header against England in 2006 and within a year of making his move to English side Middlesbrough who had been promoted to the Premier League.
The English side had lost both Mark Viduka and Yakubu in the same transfer window so they badly needed to replace those goals while trying to avoid relegation from the England's top flight league.
On deadline day in 2008, in a desperate search for goals, they secured the signing of the Brazil international from Dutch side Heerenveen for €20 million, on a four-and-a-half year contract.
Alves had a decent time in the Eredivisie as he found himself on the score sheet 45 times in just 39 league games before his move to the Riverside Stadium.
However, the forward struggled to adapt to the English style of football. His first two goals for Middlesbrough came at the Riverside Stadium on the 6th April against Manchester United in a 2–2 FA Cup draw. He finished his first season in England with a hat-trick in an 8–1 home victory against Manchester City.
Alves could not find the form which led to his record move. In his first season he managed just 7 goals in 33 games. 14 games and 6 league goals in his second season turned out to be an even bigger disappointment and lead to the Teesiders being relegated from the Premier League back down into the Championship.
July 2009, along with team mate Mido, the Brazilian went AWOL and missed pre-season training ending his dismal spell at the Riverside with Middlesbrough selling him to Qatari side Al-Sadd of Qatar for a fee of £6m.