Tottenham have made some wily transfer dealings over the years. Signing Luka Modric for £16.5m and selling him to Real Madrid for double. Turning a total of £7m paid for Gareth Bale into £85m, with Madrid again shelling out.
Sadly for Daniel Levy, not every deal can turn out as well as Christian Eriksen costing a puny £13.5m. Spurs (opens in new tab) have been just as guilty of splashing the cash on a load of old rubbish as anyone else.
Here are Tottenham's 15 worst signings of the Premier League era.
15. Sergei Rebrov
Rebrov formed one of the great strike partnerships in European football at Dynamo Kyiv playing alongside Andriy Shevchenko, and remains the Ukrainian Premier League all-time top-goalscorer.
Yet while Shevchenko went on to terrorise defences all over the continent for Milan (opens in new tab), winning the Scudetto and the Champions League, Rebrov struggled massively.
Nine league goals in his opening season wasn’t good enough for a player who cost £11m, and by the time he left north London for Fenerbahce he’d only found the net on 10 occasions in 59 Premier League appearances.
14. Bobby Zamora
Zamora managed just 16 Premier League appearances, 10 of which came off the bench, after signing for Glenn Hoddle’s Spurs in summer 2003 following three prolific seasons with Brighton (opens in new tab).
He didn't score a single league goal in a Tottenham shirt; in fact, the only time he scored in the single season he spent in north London was in the League Cup, where he netted the winner against future employers West Ham (opens in new tab).
There was no doubting Egyptian striker Mido’s ability to score goals, and his loan move from Roma (opens in new tab) to Tottenham for the duration of the 2005/06 season was no different.
Things went wrong after that loan deal was made permanent at the end of August 2006, though, with the 2006/07 campaign yielding just one Premier League goal in 12 appearances.
Martin Jol had paid just over £6m for the former Zamalek goal-getter’s signature, but managed to offload him to Middlesbrough for a profit a year later.
12. Roberto Soldado
Following the world-record sale of Gareth Bale in summer 2013, Tottenham broke their transfer record three times.
First they signed Paulinho for £17m in early July, before bringing in Soldado from Valencia for a fee of £26m (Erik Lamela signed for £28m later that summer).
Soldado worked hard for the team but seemed incapable of scoring goals – precisely the reason Spurs had spent the best part of £30m on him for. Of the seven players Spurs brought in with the Bale money, only Lamela and Cristian Eriksen could be considered successes.
11. Kevin-Prince Boateng
Boateng chose Tottenham over Sevilla (opens in new tab) and joined ahead of the 2007/08 season from hometown club Hertha Berlin. He cost Spurs more than £5m but only made 24 appearances in the 18 months he spent at White Hart Lane, before departing on loan to Borussia Dortmund (opens in new tab) in the January transfer window in 2009.
Boateng would have his revenge, though, scoring the winning goal in the 2010 FA Cup semi-final against Tottenham to fire Portsmouth into the final, where they were beaten by Chelsea (opens in new tab).
10. Calum Davenport
Davenport joined Spurs in 2004 following three good seasons with Coventry in the lower leagues. Tottenham spent £1.3m on his signature but he only played a total of 16 Premier League games in three years at White Hart Lane, with the defender spending much of his time out on loan at West Ham, Southampton (opens in new tab) and Norwich.
Davenport joined the Hammers on a permanent deal in 2007 but struggled to settle at Upton Park, and was forced to quit the professional game three years later after being stabbed.
9. Vlad Chiriches
Romanian defender Chiriches was one of the Magnificent Seven brought in during the summer transfer window in 2013 after Gareth Bale left for Real Madrid (opens in new tab). It started so well for the defender following his £8.5 move to north London, with Tottenham conceding just twice in his first nine appearances for the club.
It was all downhill from there, though, culminating in Spurs selling him to Napoli (opens in new tab) in 2015 after 41 appearances in all competitions. Chiriches never really convinced in the heart of the Tottenham backline after a solid start.
With all the incredible footballing talent Brazil has produced over the years, Spurs somehow managed to end up with Sandro, Paulinho, Heurelho Gomes and Gilberto.
The left-back joined from Hertha Berlin following four years in the Bundesliga and arrived with a good reputation, having represented his country at the World Cup in 2006 and won the Copa America a year later.
Yet when he left Spurs a little over a year after signing, he’d played only a handful of matches and been substituted off at half-time in three of the seven games he'd started.
7. Ilie Dumitrescu
One of Ossie Ardiles’s ‘Famous Five’, Dumitrescu signed for Spurs in summer 1994 following Romania’s sensational showing at the World Cup in the USA.
That great Romanian side, which featured the likes of Gheorghe Hagi, Gheorghe Popescu, Ioan Lupescu and Dan Petrescu, reached the quarter-finals thanks to Dumitrescu's two goals against Argentina.
After a bright start at the Lane, scandal soon followed when the News of the World published a story alleging Dumitrescu had used a prostitute in London. He was swiftly loaned out to Sevilla for the rest of the season, before being sold to West Ham.
6. Mbulelo Mabizela
The South Africa international so impressed in a pre-season fixture for Orlando Pirates against Tottenham in summer 2003 that Spurs decided to buy him. But after just one year, nine appearances and numerous disciplinary issues, the defender was told to seek employment elsewhere.
After leaving Tottenham Mabizela was handed a trial at Fulham (opens in new tab), who decided against signing him due to weight issues. A title-winning stint in Norway followed before he returned home to South Africa in 2006, where he’s been ever since.
5. David Bentley
It’s hard to reconcile the fact that Tottenham once spent £17m on Bentley – and only managed to get 62 matches out of him in his five-year association with the club.
Loan spells at Birmingham, West Ham, Blackburn and most bizarrely, Rostov in Russia failed to reignite Bentley’s career, and he retired from football at the age of 29 in 2013, saying he'd fallen out of love with the modern game.
The winger did score a particularly memorable goal in a north London derby against Arsenal (opens in new tab), volleying the ball past Manuel Almunia from 45 yards. That, sadly, was his only real contribution to the Tottenham cause.
4. Paolo Tramezzani
Everything about the Tramezzani transfer should make Spurs supporters shudder. Tottenham had just avoided relegation in 1998 and Justin Edinburgh was the only left-back in the squad, meaning manager Christian Gross was desperate for reinforcements on the left-hand side of defence.
Tramezzani came in from Piacenza having previously represented the likes of Inter, Cesena and Venezia in his career, but Gross' replacement George Graham didn't take to the Italian and he was shipped off after just seven games for the club.
3. Jonathan Blondel
Belgium international Blondel made his Premier League debut aged just 18 years and 150 days in a Spurs win over Southampton in August 2002.
He was regarded as one of Europe’s top prospects at the time, having helped Mouscron to the Belgian Cup final after reportedly turning down the chance to join Manchester United (opens in new tab) six months before the Tottenham move was finalised.
Blondel wouldn’t play again in the Premier League for over a year, coming on as a late substitute in a 1-0 defeat by Bolton in November 2003 as Spurs endured an awful start to the season. He only made seven more league outings for Spurs before returning to Belgium.
2. Grzegorz Rasiak
Rasiak made his name playing for Groclin in his native Poland and was part of the team that knocked Manchester City (opens in new tab) out of the 2003/04 UEFA Cup on away goals. At the end of the campaign he signed for Championship side Derby on a free transfer, before going on to score 16 goals in his first season in English football.
Spurs signed the striker with two minutes to spare on transfer deadline day in August 2005, but it quickly became apparent that it was a move too far for the Poland international. Rasiak lasted until the following February before being moved on to Southampton.
1. Bongani Khumalo
Defender Khumalo joined Spurs in the January transfer window in 2011 from Supersport United in his native South Africa. When he left the club four-and-a-half years later to return to the Pretoria-based outfit, he hadn’t played a single minute of competitive football for Tottenham.
He was loaned out on five occasions during his time at White Hart Lane, spending time with Reading, Preston, Doncaster and Colchester in England and playing the 2012/13 season with PAOK in the Greek Super League.
He finished his career with South African side Bidvest Wits - which probably explains why he was never cut out for life at Spurs.
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