1. Juan Sebastian Veron (Lazio – Man Utd £28.1m)
Veron arrived from Italy with a big reputation, deservedly, as one of the world’s best midfield players who was a regular in both the Lazio and Argentina sides. A creative midfielder with brilliant vision and an eye for a pass, he was good enough that United deemed him good enough to be worth the best part of £30m.
Unfortunately Veron failed to settle in the English game, finding it too fast and physical for him. Injury also hampered is United career, and despite backing from Alex Ferguson, fans and media alike blasted his performances.
He spent just two seasons in Manchester before being sold to Chelsea for £15m.
2. Juan Sebastian Veron again (Man United – Chelsea £15m)
Despite two poor seasons at United, Claudio Ranieri thought Veron could make an impression in The Premiership, and shelled out over half of what United had paid two years previously.
His Chelsea career couldn’t have started better, scoring the opener in a 2-1 win over Liverpool at Anfield on his debut.
After that game his form steadily dropped and he only played 14 times for the Blues before heading back to Italy with Inter Milan.
3. Denilson (Sao Paulo – Real Betis £21.5m)
When Denilson signed for Spanish side Real Betis in 1998 it was a then record transfer. He came with a big reputation, having performed well for Brazil in the Copa America.
After just one season Betis were relegated and he was loaned back to Brazil. Upon his return he was considered a liability by his clubs fans, a luxury player, his trademark step overs signifying style over substance.
Despite winning the 2002 World Cup with Brazil he was largely considered a failure at Betis, and was sold to PSG in 2005.
Since then he has become somewhat of a journeyman, appearing in France, Saudi Arabia, USA, Brazil, Vietnam and Greece.
4. Serhiy Rebrov (Dynamo Kyiv – Tottenham Hotspur £11m)
Another to move into a big league with a big reputation, Rebrov was one half of Kyiv’s brilliant strike partnership with Andrei Shevchenko. Rebrov was also the all-time top goal scorer in Ukrainian football, and still is.
His prolific goal scoring led to him signing for Spurs in a big money move, seen by Geogre Graham as the man to fire Spurs to glory.
Not fancied by new boss Glenn Hoddle he was farmed out on loan a couple of times, and at the end of his time at White Hart Lane had scored only ten goals in 60 games.
5. Hugo Viana (Sporting Lisbon – Newcastle United £12m)
Many foreign imports fail to make the grade in the Premier League. Some site the weather, others the style of play, the pace and physical nature, some blame
the lifestyle and the food.
Hugo Viana fits the bill of a failed foreign import. Newcastle United shelled out a hefty fee for the Portuguese youngster in 2002. He only played 39 times for The Magpies, mostly as a sub, and after three years headed back to Sporting.
6. Robbie Keane (Tottenham Hotspur – Liverpool £19m)
Rafa Benitez bought and sold a lot of players in his time on Merseyside, and many were big disappointments, none more so than the Irishman who once played for Inter Milan.
Whether he was signed as backup to Fernando Torres or as a strike partner is unclear, but after 19 games and five goals he headed back to Spurs. The same season he was sold.
A massive let down at Anfield, Harry Redknapp resigned him for £12m, making a £7m profit in six months. Since his move to Liverpool and back he has looked a shadow of his former self.
7. Andriy Shevchenko (AC Milan – Chelsea £30.8m)
Perhaps the most expensive transfer flop of all time, Shevchenko came to Chelsea with a huge reputation after winning trophy after trophy with a brilliant AC Milan side.
But perhaps it was done above Jose Mourinho’s head, as Sheva was said to have been Chelsea chairman Roman Abramovic’s favourite player.
Either way, he never re-created his Milan form, and scored just nine goals for Chelsea, and three years later was back at Dynamo Kyiv.
8. Francis Jeffers (Everton – Arsenal £8m)
Not the most expensive on this list by a long way, he was one of The Gunners most expensive ever signing when he arrived at Highbury in 2001.
A hot prospect from Everton where he had scored 18 goals in 49 games, he was signed by Arsene Wenger to be a typical English goal scorer.
His time was at Arsenal was marred by injury, and the form of Sylvain Wiltord and Thierry Henry. His goal tally never reached double figures for Arsenal and two of his goals came against Farnborough in the FA Cup.
Despite all this, his goal to games ratio for England comes in at a very impressive one goal every 45 minutes.