The Brazilian goalkeeper was signed for about £8m from PSV Eindhoven in 2008, but his ridiculous mistakes between the sticks led to the nickname 'Hilarious Gomes'. The Brazilian stopper never justified his price tag, and was released last summer having become third or possible fourth choice at White Hart Lane.
Signed as a replacement for Sol Campbell in 2001, the £1.4m arrival from Red Star Belgrade never truly adapted to English football. Having struggled to impress at centre back, Bunjevcevic was released in 2006, ending his career in the Netherlands with ADO Den Haag. The money wasn't terrible, but Bunjevcevic was.
Snapped up for £3.3m from Benfica, Rocha was another centre back who just found it hard to acclimatise to life in England, and played just 18 games in three years for Spurs before moving on to Standard Liege. Another remarkable waste of money for Tottenham.
£5m. That's what Tottenham paid to bring left back Ben Thatcher to White Hart Lane from Wimbledon, and his time with Spurs was a disaster. The Welshman was incredibly limited for the price tag, and played just 46 games in three seasons before being flogged to Leicester City in 2003 for just £300,000.
After being named the best left back in the Bundesliga, Spurs paid £2m to land Brazilian international Gilberto from Hertha Berlin. Seven appearances in 18 months just goes to show what a calamitous signing Gilberto was for Tottenham, who was swiftly sent back to Brazil with Cruzeiro.
Another signing from Red Star Belgrade, another failure. Slovenian playmaker Acimovic arrived on a Bosman from the Serbian side, but played just 17 games in two seasons - which included a stunning miss against Fulham in 2003, where Acimovic contrived to miss when it was so, so much easier to score.
After impressing with Blackburn, Bentley was touted as the next great England winger - which prompted Tottenham to fork out £15m to sign him in 2008. Barring an outstanding long range goal against his former club Arsenal, Bentley's time with Spurs was terrible, playing just 62 games, contributing only six goals and nine assists. The 30-year-old is now without a club in a career of 'what could have beens'.
In a deal which cost around £7m, Tottenham landed one of the top up and coming strikers. Helder Postiga arrived from Porto as a 21-year-old coming off a season where he hit 19 goals, but he found the net just one in his solitary season at White Hart Lane before Spurs sent him back to Porto in exchange for midfielder Pedro Mendes.
Ukrainian goal machine Rebrov arrived at Tottenham having been prolific with Dynamo Kiev, but he simply couldn't repay the £11m Spurs paid for him. 15 goals in 75 games was a meagre return for Rebrov, who couldn't find any success again until he returned to Kiev in 2005.
Now to one of the most ridiculous Spurs transfers in recent history. Then-Tottenham boss Martin Jol was desperate for a striker on deadline day in 2005, and after watching Rasiak score 18 goals in his solitary season at Derby County, the Polish target man completed a £3m move to North London. Yet he played just eight games for Spurs before moving on to Southampton just six months later with no goals for Spurs.