OTP revisits some of the transfers that the country’s largest clubs would rather forget…

10. Heurelho Gomes
While the Brazilian has played almost 100 games for Spurs, he still makes our list. He cost a staggering £10million, and the fact that Spurs bought a 39-year-old to replace Gomes in the short-term does not give out the best messages. AVB is also reportedly looking for a longer term replacement.

9. Sebastien Bassong
Fans of Newcastle will tell you that Bassong was an accomplished defender on Tyneside, earning a big money move to Spurs after the club’s relegation. In the capital, however, things have just not worked out. The Cameroon international has played less than 50 league games in three seasons, finding himself behind King, Dawson and Kaboul. For £8million, he should be first choice.

8. Ilie Dumitrescu
We have left his fellow countryman Popescu off this list as he was sold to Barcelona for profit, but Dumitrescu had a woeful time at White Hart Lane. Early in his Spurs career, Dumitrescu was forced to deny rumours that he chased prostitutes. Spurs loaned him out to Sevilla whilst the stories died down, but it was not exactly an ideal start. He played for half of the 1995/6 season on his return from Spain, but was sold to West Ham after just four league goals.

7. Jason Dozzell
Often chosen in lists to find Spurs’ worst ever player, Dozzell was signed for £1.9million from Ipswich. He played 32 league games in his first season but scored just 14 goals in four seasons, a poor return for England’s star of the future (I know that sounds ridiculous now). He was loaned back to Ipswich briefly before moving permanently to Northampton Town.

6. Helder Postiga
He would have been much higher up this list if Spurs hadn’t managed to regain much of their original outlay when selling the striker to Porto. An upcoming star within European football, Postiga simply never clicked, scoring just one goal in the league throughout his sole season in England, despite the club paying £6.25million for his services. Still known for missing chances, but now in international tournaments.

5. Ben Thatcher
Paying £5million for a passing, cultured centre back is understandable, as they almost perform two roles within a team. But paying £5million for a Wimbledon thug who would then play just 36 league games in three seasons before moving for a paltry £300,000 is not cool. Spurs should be ashamed of themselves.

4. Giovani dos Santos
If Barcelona are allowing a young player to leave, it is probably because he isn’t all that, and so it has appeared at White Hart Lane, where the £4.7million Mexican has made 17 Premier League appearances (two starts) in four years, even being loaned to Ipswich in that time. Frustratingly, he continues to perform admirably for his national team.

3. Ramon Vega
He became a symbol of the dodgy central defender in the late 1990s; a benchmark against which other defensive flops could be measured. He stayed for four years but never maintained a first-team place after a £3.75million move from Italy. He finally moved on loan to Celtic in his final season, and was released by the club after Celtic rejected an offer to take him permanently.

2. David Bentley
OTP is not sure which of the three things are more surprising: that Spurs thought it a good idea to spend £15million on Bentley, that he has seven England caps or that his stock has fallen quite so far. He has only played a part in 10 league games a season since his move from Blackburn (and only twice since the summer of 2010). Last season the big money England international was loaned to the Championship.

1. Sergei Rebrov
Everyone’s second favourite Meerkat-lookalike footballer was 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 one goal in thirty games the following season. Loan spells followed, and then a one-year-deal with West Ham after Spurs let his contract expire. Still looked dreadful there.

Have we missed your favourite worst Spurs signing? Let us know below.