19) Ricardo Rocha (Benfica to Tottenham – £3.3m – 2007)
Hardly the most expensive signing but the centre-back was a fully-fledged Portuguese international when he first arrived at White Hart Lane and big things were expected of him.
However, Rocha just couldn’t cut it in the Premier League. He struggled with the pace of the game, and he left after three forgettable seasons. He did, though, go on to have a somewhat more successful spell at Portsmouth.
