#2 Sean Dundee (Liverpool)
A look at their transfer dealings would make one believe that Liverpool had the knack of making ridiculous transfers under the aegis of Gerard Houlier and Roy Evans. The club had been thrown into a rather difficult situation at the beginning of the 1998-99 season when Robbie Fowler incurred a long-term injury and was believed to be out until at least winter.
The side were desperate to bring a striker to the Merseyside so as to add to the side’s attacking options and decided it was in the best interest of the side if they forked out £2 million for Sean Dundee, a man who had 60 goals in 115 appearances for Karlsruher SC and TSF Ditzingen.
Dundee arrived at Liverpool claiming to be faster than their golden boy at time Michael Owen but failed to live up to his claims. He failed to break into the side even when the regular striker at the club, Owen, was injured and never started a game for the Reds. He made just 3 appearances for the Reds, all of them as substitutes and needless to say never managed to score for the Reds.
He returned to Germany at the end of his one and only season on the English soil when he signed for VfB Stuttgart and to this day, is believed to the worst signing in the history of the club and that is quite a feat when you consider have signed the likes of Paul Konchesky, Andy Voronin and El Hadji Diouf amongst a host of other players who failed to live up to their billing.