

Bongani Khumalo - £1.5m (from SuperSport United, 2010) In the 2008/09 season he started just two games and was brought off at half-time in both. He was unable to get to grips with life in North London and would ultimately only play seven league matches in 18 months. Gilberto did indeed have a good reputation when he signed for Tottenham, having represented Brazil at the 2006 World Cup. He was substituted at half-time in that game after gifting PSV the only goal, though manager Juande Ramos insisted it was due to a lingering injury that he was brought off. Gilberto - £3m (from Hertha Berlin, 2008)Ī January transfer window signings from Hertha Berlin in 2008, Gilberto became the first Brazilian to play for Tottenham at senior level after making his debut in a UEFA Cup fixture against PSV. Here are 10 of the worst signings in Tottenham's history. However, while shrewd deals like ones for Christian Eriksen and Huge Lloris have taken place, there have also been several transfers that haven't hit the mark. Sancho and the five players Man Utd must keep this summer
