6. Sergei Rebrov
He expected to be an equivalent to Shevchenko when he arrived at Spurs from Dinamo Kiev, but turned out to be more of a Voronin. He started with a struggling nine goals in 29 games, where he looked off the pace, and then scored just one goal in thirty games the following season.
His performances wasn’t good enough for a player who cost £11m, and by the time he left north London for Fenerbahce he’d only found the net on 10 occasions in 59 Premier League appearances.
5. Grzegorz Rasiak
Grzegorz Rasiak is the definition of a panic buy; brought in by then Spurs boss Martin Jol to score a heap load of goals, Rasiak did the complete opposite.
Lured from Derby County on transfer deadline day in 2005 with the club in desperate need of attacking reinforcements, Rasiak failed to score in nine appearances for the club and was shipped out on loan to Southampton just a year later, before eventually completing a permanent move.
4. Helder Postiga
Helder Postiga came to Spurs full of hope from Portuguese giants Porto in 2003. However, he proved to be £8.5 million down the drain, scoring just 1 goal in 19 games for the Lilly Whites.
Postiga was swiftly sent back to his former club Porto in exchange for Pedro Mendes. He will always be remembered among the worst Tottenham Hotspur signings ever.