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With all the money that's been thrown around and wasted in the world of football over the years it's no great surprise that there's a whole catalogue of terrible transfers. So here's our list of some of the worst transfers in football history, a list that will undoubtedly grow and grow as managers, chairmen and clubs continue to throw their money away chasing the dream of finding that guaranteed 30 goal-a-season striker, or that 'new maradona', only to find they've just spend their pounds or euros on a complete donkey, or a homesick player with an attitude problem.

You may also find some of these in our list of the best and the most bizarre transfers.

Year, Player Details
2009
Roque Santa Cruz

Blackburn Rovers to Man City (£17.5m)
Man City Santa Cruz had been a surprising success at Blackburn under Mark Hughes so it was not surprise when Sparky tried to sign him after being named manager at the now mega-rich City. Hughes had a couple of bids turned down in the winter of 2009 but eventually got his man in June 2009 for a whopping 17.5 million quid. It seemed a lot of money at the time but a year later and with just a handful of starts under his belt and a paltry 3 goals to his name it looked truly dreadful ! With injuries hampering him it was rumoured in the Autum of 2010 that the Paraguayan would be heading out of the club, which would make the transfer fee cost City about a million pound per appearance. Nice.
2008
Robbie Keane

Spurs to Liverpool (£20.3m)
Liverpool Dont' get us wrong, we like Robbie Keane, unlike many modern players he seems quite down to earth and normal. He comes across as the sort of bloke who you could have a decent natter with down the pub without there being any danger of him winding you up, bragging about how great he is, how fit his wag is and how many Ferrari's he's bought since breakfast. But fair's fair, his transfer to Liverpool goes down as a stinker. Nicely settled at Tottenham for 6 years, his time at White Hart Lane had seemingly come to a bitter end after Liverpool's public pursuit of the player in the summer of 2008. Not even a vast transfer fee of £20 million and the knowledge that Keane was wanting to move to his childhood favourites was enough to placate many of the Spurs fans. However, just 6 months later the player was on his way back to the luvverly Cockerney lap of Harry Redknapp, having scored just five league goals for the Anfield club. According to the increasingly bemused Rafa Benitez, Keane's style hadn't fit into the teams as anticipated and the spaniard decided that a move away was the best for all concerned. Quite bizarre really, considering that Liverpool were challenging for the title at the time and Benitez had no replacement lined up, putting yet more pressure on a tired looking Fernando Torres. Oh yes, and Rafa effectively lost £8million on the deal, not bad going for someone who had been pleading poverty with the club's owners for the previous couple of season's.
2007
Afonso Alves

Heerenveen to Boro (£12.7m)
Boro At the end of the Dutch 2006-07 season Alves had scored 34 goals in the Eredivisie for Heerenveen and became the 3rd Brazilian after Romario and Ronaldo to top the Dutch scoring charts. He was also a whisker away from claiming the European Golden Boot award, missing out by just a single point to Roma's Francesco Totti. When he started the following season in similar fashion and blasted 7 (that's seven) goals in a 9-nil thrashing of Heracles, he was hot property, and Heerenveen were expecting a number of high bids for him in the January transfer Window. It was therefore something of a surprise when Boro signed him at the last minute for a club record 12.7 million. He scored a respectable 6 goals in 11 Premier League outings that season, inclucing a hat-trick in the 8-1 thumping of Man City. However, the 2008-09 season was a different kettle of fish, Alves scored early on in the season but then really struggled, notching just 4 goals in 31 Premier league outings as the north-east club were relegated to the Coca-Cola Championship. At the start of the next campaign Alves and his massive wages were offloaded to Qatar side Al-Sadd for an undisclosed fee.
2006
Andriy Shevchenko

AC Milan to Chelsea (£30.8m)
Chelsea It's a crying shame when you have to put a footballing legend on the worst transfers list, but on it has to go... The Ukranian striker had scored nearly 130 goals in just over 200 games for AC Milan when Chelsea tok him to West London, an incredible goal-scoring feat against the crack defences of Serie A. Chelsea's sugar daddy Roman Abramovich had been sniffing around him for a while, and there had been persistent rumours for over a year that a switch was inevitable. So it was no surprise when a deal was announced in the summer of 2006, although a few jaws dropped when the fee was disclosed - 30.8 million pounds for someone just a few months shy of his 30th birthday. At first it looked like it could actually be a marriage made in heaven - unlike many of Chelsea's other high-profile purchases such as Crespo and Drogba, Shevchenko sounded like he genuinely fancied the move to London, scoring on his debut in the Charity Shield and notching his first premiership goal before August was out. However, despite chipping in with occaional goals throughout the season he never managed to get on a sustained scoring run, and also finished the season injured. 2007-08 was even worse, with a constant stream of injuries and rumours of a poor relationship with boss Jose Mourinho. Despite a change of manager and the fans and owner still wanting him to succeed, Shevchenko was loaned back to Milan for the 2008-09 season, not that it changed his luck much, just 9 starts and 2 goals was not how the Rossoneri wanted to remember him.
2003
Claude Makelele

Real Madrid to Chelsea (£16.8m)
City From a Real Madrid point of view the sale of Makelele to Chelsea has to go down as one of the worst transfer decisions in football history. In the summer of 2003 the French holding-midfielder had firmly established himself as one of Real's key players. With 2 La Liga titles and a European Cup winners medal stuffed in his pocket, everyone from the fans, to the media, to the players, could see that Makelele allowed the 'Galacticos' in the team to strut their stuff, safe in the knowledge that he was there to pick up the pieces behind them. Everyone that is, except the people handing out the wages. As one of the club's lowest earners he eventually dared to ask for a rise, and when it was turned down flat by club President Florentino Perez, Makelele handed in a transfer request. Perez accepted it and then mocked the Frenchman, claiming that he had no skill, no speed, could only pass the ball sideways or backwards, and that he would not be missed. And so when Perez got the news that there were some new rich kids in town, called Chelsea, who couldn't wait to get their grubby little hands on a holding midfielder who "couldn't pass more than 3 yards", and were prepared to pay nearly £17m for him, the Real President nearly choked on his paella. The fool. By the time Perez resigned three and a half Galactico-filled years later, the club had not won a single trophy. Makelele meanwhile, started his English medal collection.
2003
Luciano Figueroa

Rosario Central to Birmingham City (£2.5m)
City A much heralded signing at the time, Steve Bruce thought he'd managed to unearth a real diamond when he persuaded the 22 year old striker to swap Santa Fe for the West Midlands. And when everyone saw the young Argentine's stats (top scorer in Argentina the previous season with 17 goals in only 19 games, 35 goals in 57 appearances overall) they were inclined to agree. But as most Premiership managers know, a phenomenal scoring rate abroad means diddly squat when you arrive in good old Blighty. And as soon as someone uttered the phrase "new Batistuta", it was always going to end in tears. Things started to go wrong immediately - Spanish club Osasuna claimed they'd actually signed him a month earlier, despite having no documents to support their protests. Whether this explained his incredible form for 'the Blues' (no goals in 1, that's one, appearance) who knows, but Figueroa was soon farmed out on loan to Mexican club Cruz Azul. Obviously, as soon as he left Birmingham airport he began to find his form again, netting 11 times in 19 games, before transferring permanently to Villareal.
2002
Vicente Matias Vuoso

Independiente to Man City (£3.5m)
City Vuoso moved to Manchester at around the same time as his Independiente strike partner Diego Forlan. And whilst Forlan eventually achieved almost cult-status in the red half of the city, the blue half never even found out what Vuoso looked like. 0 goals in 0 games - it seemed to sum up the erratic transfer policy of City's manager Kevin Keegan, but hey - at least the youngster had a 100% record. Within a year he was gone. Fans of Mexican club Santos Laguna wondered what the hell they'd done to deserve such a loan-signing as this, but they were soon choking on their Guacamole as Vuoso went from the ridiculous to the sublime, bagging more than 50 goals in 100 games for the club after his move was made permanent.
2001
Francis Jeffers

Everton to Arsenal (£8.0m)
Arsenal With Michael Owen bursting onto the football scene across Stanley Park in 1997, Everton could hardly believe their luck when one of their own youngsters followed suit a year later, as Francis Jeffers, the 18 year old with the sticking out ears, scored 6 times in 15 appearances in the 1998-99 season. When Franny followed it up with a similar scoring rate in the next two seasons, Arsenal manager Arsene Wenger decided to persuade the Goodison club to part company with their prized asset... a couple of Chinese burns and a suitcase stuffed with 8 million 1 pound coins later, and the deal was done. Everyone was happy - Everton had a large sum of cash to waste on David Ginola and Niclas Alexandersson whilst Arsene Wenger had signed the now legendary "fox in the box". Jeffers scored goals for fun in the England U21 set-up, his 13 goals equalling Alan Shearer's national record. However, injuries and just 2 goals in his first season was hardly the return that the Highbury faithful was expecting, and another 2 in the next season meant he was sent packing back up t'north to Everton to try and recapture some form. He didn't. He did manage to grab a goal on his England debut in that dreadful defeat to Australia, meaning he has an England goal per game ratio the envy of many, but just one goal back at Goodison and a disagreement with David Moyes meant that Jeffers was sent packing, the only surprise being that the Gunners somehow recouped o2.6m for him from Charlton. And people wonder why Wenger doesn't buy English talent.
2001
Nicolas Medina

Argentinos Juniors to Sunderland (£3.5m)
Sunderland Anyone remember a football documentary a few years back, showing a hapless Peter Reid leafing desperately through an international football yearbook, hoping to find some talented foreigner that he could entice to the Stadium of Light with a trail of Scooby-Snacks and a promise of first team football ? Did we dream it ? Possibly not when you think back to the Nicolas Medina saga. "The complete midfield player!" exclaimed Peter Reid to an excitable Wearside public. Unfortunately, only those present at an FA Cup tie with Bolton saw exactly how complete he was. Despite Sunderland battling against relegation Medina never played a single league game and eventually moved back to South America, a genuine 3.5 million Premiership flop.
1999
Rafael Scheidt

Shite
Gremio to Celtic (£4.8m)
Celtic Rival Rangers fans were rubbing their hands in glee when they heard how his surname was pronounced (shyte) following the Brazilian's £4.8m move from Gremio in December 1999. And after Celtic's fans had seen him in action for the first time the general consensus was that that he was Scheidt by name but shite by nature. It was rumoured that Celtic's manager John Barnes had signed him without anyone at the club having seen him play, and given the reports of just how bad he actually was this is most probably the case. Horrified by the cold, wet, Scottish winter, baffled by talk of deep fried Mars bars, and hampered by injuries, it's no wonder he struggled to settle in. He started only one league game that season and was quickly substituted half-way through it. Yet when Martin O'Neill took over the following summer he quickly stated that everyone started with a clean slate, even Scheidt. That promise lasted exactly one pre-season game though - after witnessing the hapless Brazilian being given the runaround by a couple of local Irish lads O'Neill packed him back off to Brazil on loan. At least Rafael's transfer produced one of our favourite quotes... "He couldn't trap a bag of sand". Strangely, he did manage to get 2 full caps for the Brazilian national team, something that wont surprise Leeds fans seeing as though Roque Junior received nearly 50.
1998
Stephane Guivarc'h

Auxerre to Newcastle Utd (£3.5m)
Newcastle Signed by Kenny Dalglish in the midst of some wholesale re-building, the Geordie faithful started to worry when they caught sight of the wretched Frenchman during that summer's world cup. Despite somehow grabbing hold of a winners medal, the French striker contributed little throughout the tournament, and it now seems almost unthinkable that he was consistently picked ahead of Thierry Henry. One of Guivarc'h's main critics during the tournament had been tv pundit Ruud Gullit, and in a great twist of fate, Dalglish was sacked at the start of the season and replaced with... Ruud Gullit. Despite scoring on his debut against Liverpool, the hapless Frenchman's days were numbered. And weren't the Geordie fans relieved. Considering him overpaid (16k a week anyone ?), lazy, and sick of him lording it around the Bigg Market with his winners medal round his neck, they began to jeer him home and away. To their relief, and surprise, they somehow managed to offload him to Rangers for the same fee, although the Glaswegians would ultimately have the last laugh by selling them fellow French funnyman Jean Alain Boumsong for a whopping 8million big ones.
1996
Ali Dia

Unattached to Southampton (Trial)
Southampton FC Ali Dia, or Ali Dire as he became known, will go down in history as possibly the worst ever Premiership player, but also the cheekiest. Having struggled to make a living in the lower reaches of French football, the 30 year-old Dia turned his attention across the English Channel, where, with the help of BSkyB, the roads to football stadiums had become paved with gold. Turned down by Bournemouth and Gillingham, he managed to sign semi-pro terms with non-league outfit Blyth Spartans, which was probably just about his level. However, the ambitious Dia wanted more, so armed with a cunning plan he set about making the step-up to the Premiership. And Southampton's manager Graeme Souness was on his radar... Dia pretended to have won 13 caps for Senegal (he hadn't) and that he was related to top Liberian striker George Weah (he wasn't). However, a phone call from Weah was enough to convince Souness to hand him a 30 day contract. Dia was lined up to play in a reserve game, but after it was cancelled he was thrown straight into the deep-end with a place on the bench against Leeds in November 1996. When Le Tissier was injured after half an hour there was high expectation in the crowd as the new signing, the cousin of the great George Weah, came on to a rapturous welcome. And what a debut it was - 50 spectacularly bad minutes later, the likes of which has not been since anywhere in professional football, Dia was himself substituted in front of a disbelieving Dell crowd. It later transpired that the crackly voice on the other end of the phone hadn't been the AC Milan legend Weah after all but Dia's agent. Southampton cancelled his contract, Gateshead snapped him up for some publicity, and he hasn't been seen since. Or has he ? Did anyone double-check Jean-Alain Boumsong's details ?
No video clip of the great man in action, but click here for Matt Le Tissier's view.
1995
Marco Boogers

Marco
Sparta Rotterdam to West Ham Utd (£800,000)
West Ham When people start talking about 'Arry Redknapp being the finest wheeler'n'dealer in the land they're obviously blissfully forgetting some of his debacles from the 90's. Whilst 'Arry was doing a sterling job with the academy and bringing through the likes of Ferdinand, Lampard, Cole and Carrick, handing him the club chequebook in those days meant there was a good chance things might go all apple'n'pear-shaped, because for every Paulo Di Canio signing there was a Florin Raducioiu, or worst of all... a Marco Boogers. The Dutch striker, aged 28 and in the prime of his football life, arrived in the summer of 1995 from Sparta Rotterdam for £800,000 but was gone by the end of the winter. His debut was bad (subbed before an hour) but was a veritable success compared to his 2nd game - taking to the pitch as a substitute he was sent off within minutes for a horror tackle on Man Utd's Gary Neville. Such starts often leads to a player aquiring cult status, but not Marco. He famously did a runner back to Holland and was eventually found in a caravan park - a gibbering wreck who couldn't face his Hammers team-mates. A few month's later he was farmed out to FC Groningen on loan, where, remarkably, he managed to get back on track and finished the Dutch season with a near 1-in-2 goal per game record - something that still mystifies the Hammers' fans almost as much as the idea that Harry actually paid money for the Dutch fruitcake.
1979
Steve Daley

Daley
Wolves to Man City (£1.47m)
Man City September 1979, and Man City boss Malcolm Allison is about to make British transfer history by blowing the biggest barrel full of cash yet seen in these isles on an average box-to-box midfielder from Wolves called Steve Daley. Legend has it that a mix up between Allison and City chairman Peter Swales ended with the latter offering £1m more than Big Mal was expecting (something Swales denied), and strangely Wolves spent exactly the same amount of money bringing Andy Gray from Aston Villa on the same day. On the Maine Road pitch, Daley brought new meaning to the word mediocre and less than 2 years later he was packed off to the NASL, joining Seattle Sounders for a measly 300k. Hats off to him though - despite being the butt of many a football joke during this era he was always willing to laugh about it, and when celebrity Man City fan Nick Leeson (you know, collapser of Barings Bank) backed him as the worst waste of money in a Guardian top 10, Daley replied "At least I got away with it, unlike that tw*t!". Good call Steve.