#1 Ali Dia
Ranked as the worst transfer by The Times and many leading newspapers, it is not surprising to find Ali Dia on this list in the spot of number 1. As compared to our other candidates, Dia was not even a proper professional footballer. It is believed that he had tricked the-then Southampton manager, Graeme Souness into signing him.
Souness has said that it was the legendary George Weah who had called him personally and had told him that Dia was his cousin and that he had played for Paris Saint-Germain and had also made several appearances for his country. Instead, it is believed that it was actually a fellow university student of Dia who had actually called Souness and tricked him into signing Dia.
Days later, Dia was signed and he made his one and only appearance for Southampton against Leeds United. He was brought on as a substitute for Le Tissier in the 32nd minute. But he was so bad that he was taken off in the 85th minute, ending his short debut. Shortly afterwards, he was released from his contract by the club. Dia continued to play non-league football for sometime after that but later gave up football altogether.