3. Milenko Aimovi
Making 18 appearances in total and scoring absolutely zero goals from his attacking midfielder position, Milenko Acimovic was a massive Slovenian flop. He went from making the odd appearance in his first season to being a fringe player in his second. He had performed very well for Red Star Belgrade prior to his move and had a good run in the Slovenian national side at two major international competitions (the 2000 European Championships and the 2002 World Cup), but he simply didn't perform at Spurs after joining in the 2002 summer transfer window. Acimovic moved to Lille in France and did well there, before moving to Al-Ittihad in Saudi Arabia and then on to Austria Vienna. He is now 36 and has been retired for three years. The only shining light of his horrific spell at White Hart Lane is that he cost Tottenham nothing.