The 30 strangest transfers in football history, featuring Liverpool and Real Madrid

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The January transfer window has slowly rebooted in 2020.

While there hasn't been much to talk about this year, the first month can often spark some strange moves - take Andy Carroll to Liverpool to Alexis Sanchez to Manchester United, for example.

But some of the most entertaining moves aren't necessarily those involving the biggest sides and the heftiest transfer fees.

It's a theory that the Independent have sought to test this month by counting down 30 of the weirdest and whackiest transfers in the history of world football.

From World Cup winners moving to promoted sides and West Ham players progressing to Real Madrid, there's been plenty of eyebrow-raising deals, so check out the final 30 down below:

1. Ricardo Villa and Ossie Ardiles to Tottenham

When you've just won the World Cup, signing for a newly-promoted First Division club seems a pretty strange decision, but that's exactly what the two Argentine heroes plumped for in 1978.

Barring Ardiles being shipped out on loan for the Falklands War, it proved to be a fruitful relationship that reaped two FA Cup titles, including Villa scoring arguably the greatest goal in Spurs' history.

Spurs Players

2. Roberto Mancini to Leicester City

The eventual Manchester City boss made his Premier League debut at the age of 36, failing to last the whole 90 minutes, and made just three appearances for the Foxes before hanging up his boots.

Roberto Mancini  X

3. Louie Barry to Barcelona

To be fair, it's not everyday you see a rising West Brom talent move to the Nou Camp, but Barry's Spanish fairytale looks to be coming to an end with a Midlands return to Aston Villa on the cards.

The Otten Cup - Eindhoven

4. Gennaro Gattuso to Rangers

You've got to credit Gattuso for taking the risk of swapping Perugia for Rangers at the tender age of 19 and he was greeted by Paul Gascoigne defecating in his socks. Ah well, it worked out in the end.

Rino Gattuso and Tommy Boyd

5. Julien Faubert to Real Madrid

You know it's wacky signing when Paul Merson is announcing: “His agent should be knighted by the Queen."

Faubert was sensationally air-lifted from a middle-of-the-road West Ham side for a loan spell where he shared a dressing room with Fabio Cannavaro and Raul, making just two appearances.

Real Madrid's French midfielder Julien F

6. Steven Caulker to Liverpool

We're not sure what's weirder: the fact Jurgen Klopp took the former England defender on loan from Queens Park Ranger or the fact he proceeded to play him as an auxiliary striker? We're at a loss.

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7. Alejandro Sabella to Sheffield United

The Blades rather ambitiously tried to sign some bloke called Diego Maradona - who the hell is that guy? - but were forced to settle for his Argentina teammate Sabella to the tune of £600,000.

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8. Javier Mascherano and Carlos Tevez to West Ham United

Imagine being some of the most talented players in South American football and deciding that you want to break into the European game by signing for... West Ham.

This bizarre transfer eventually culminated in spells at Juventus, Barcelona, Liverpool and Manchester United for each player, but just don't go reminding Sheffield United fans about it.

West Ham United Press Conference

9. Juninho to Middlesbrough

There was similar bewilderment when Juninho plumped for 'Boro despite having the pick of clubs at Sao Paolo and he enjoyed his time in the north-east so much that he returned twice.

Bolton Wanderers v Middlesbrough

10. Jay Jay Okocha to Bolton

Clearly some players have a soft spot for obscure English clubs and Okocha helped guide Bolton away from relegation, as well as scoring their greatest Premier League goal, after leaving PSG.

Olympique de Marseille's forward Franck

11. Fernando Hierro to Bolton

I hope whoever did the negotiating at Bolton during the early 2000s got a pay-rise, because signing a legendary defender who played alongside Ronaldo Nazario and Zinedine Zidane is no small feat.

FA Cup: Bolton Wanderers v Fulham

12. Attilio Lombardo to Palace

How do you react to reaching a second consecutive Champions League final? You sign for Crystal Palace, make 49 appearances and score 10 goals, then become their caretaker manager. Duh.

Attilio Lombardo of Crystal Palace

13. Joey Barton to Marseille

After starting World War 3 with the City squad during THAT game at the Etihad, Marseille - of all clubs - were the team to take a punt on Barton and he proceeded to clash with Zlatan Ibrahimovic.

Paris Saint-Germain FC v Olympique de Marseille - Ligue 1

14. Julio Cesar to QPR

Two years before moving to Loftus Road, Cesar was lifting the Champions League title under Jose Mourinho at Inter Milan and guarding Brazil's goal during a World Cup run to the quarter-finals.

But he decided to swap all of that for Premier League relegation, before jumping the ship as soon as times got tough for a loan spell at Toronto FC and an eventual escape to Benfica.

Tottenham Hotspur v Queens Park Rangers - Premier League

15. Edgar Davids to … every English club

Imagine swapping Inter Milan for Martin Jol's Spurs, before dropping down to the Championship and then both playing and managing Barnet in the fifth tier of English football. Mental.

Barnet v Wrexham AFC - Skrill Conference Premier

16. Bojan Krcic to Stoke City

Once deemed 'the next Lionel Messi' and one of Barcelona's youngest ever goal-scorers, you know the proverbial has hit the fan when you're signing for Mark Hughes' Stoke and suffering relegation.

Stoke City v Brentford - Sky Bet Championship

17. Luther Blissett to AC Milan

Probably the most eventful thing that happened from Blissett's spell in Italy was his quote: “No matter how much money you have here, you just cannot seem to get Rice Krispies.”

Milan thought they were signing his Watford teammate John Barnes, but instead procured a future Fakenham Town striker that went on to share a dressing room with Franco Baresi.

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18. Claudio Caniggia to Dundee

They have high standards up in Dundee. Caniggia had won the World Cup, Copa America and Copa Libertadores by the time he signed and even earned a Rangers move for his trouble.

Dunfermline v Dunde

19. Esteban Cambiasso to Leicester

Do Argentines get a kick out of signing for newly-promoted English clubs? Cambiasso became a hero at the King Power and should have stayed on an extra year for Premier League glory.

Leicester City v Queens Park Rangers - Premier League

20. Bebe to Manchester United

This is less of a strange buy and more of a terrible one. Sir Alex Ferguson broke his rule of not watching the player live before signing them and dropped his biggest transfer clanger by doing so.

Manchester United Training & Press Conference - UEFA Champions League Final

21. Kevin-Prince Boateng to Barcelona

We honestly have no idea how Barca came to the conclusion that Boateng was their man last year, especially when Erling Haland was on their radar and about 15 others strikers to boot.

The Ghanaian seemed as surprised as everybody else, was just happy to make three appearances and was booted out as soon as possible last summer. I wonder why that might be?

FC Barcelona v Real Valladolid CF - La Liga

22. Thomas Gravesen to Madrid

Swapping Goodison Park for the Bernabeu doesn't happen everyday and Gravesen's thoroughly bizarre trip to Spain saw him playing out of position and scrapping with Robinho, naturally.

Real Madrid v Cadiz

23. Christophe Dugarry to Birmingham

No offence to Birmingham, who have signed World Cup winners before, but how did they manage to land Dugarry just half a decade after he lifted football's biggest prize at France '98?

Christophe Dugarry of Birmingham City takes the ball past Craig Short of Blackburn Rovers

24. Henrik Larsson to Manchester United

This doesn't seem that strange on paper, but Larsson was past his best by the time he joined the Red Devils on loan, but three goals in 13 games meant it was a happy enough arrangement.

Manchester United's Henrik Larsson postu...

25. Jay Bothroyd to Perugia

Dashing off to Serie A after helping Coventry City get promoted is pretty exciting going, never mind when you bag seven goals from 39 games and strike up a friendship with Colonel Gaddafi's son.

Perugia's forward Jay Bothroyd (L) tries

26. Yildiray Basturk to Blackburn Rovers

The Champions League runner-up took the unusual decision to wind down his career at Ewood Park, but spending your twilight years under 'Big Sam' isn't easy and he played just 45 minutes.

Wolverhampton Wanderers v Blackburn Rovers - Premier League

27. Nicklas Bendtner to Juventus

Quite what it was about Bentdner's eight goals on loan at Martin O'Neill's Sunderland that inspired Juventus to take him on loan is anybody's guess - and only two starts came in tandem.

However, it wasn't the only bizarre striker that Juventus signed that season and picking up a past-his-sell-by-date Anelka showed they clearly didn't learn from their Bendtner gaffe.

Juventus v Torino FC - Serie A

28. Kyle Lafferty to Palermo

Lafferty's journeyman career would make for one hell of an autobiography and getting a phone call from Palermo for being "an Irishman without rules" probably takes the cake.

US Citta di Palermo v AC Spezia - Serie B

29. Papy Djilobodji to Chelsea

Remember this guy? Give yourself a pat on the back if you genuinely do, because the future Sunderland man played just 62 seconds after an inexplicable move from Jose Mourinho. 

WAC RZ Pellets v Chelsea - Friendly Match

30. Ali Dia to Southampton

It doesn't get any better than this. The sheer hilarity of Graeme Sounness signing Dia because he convinced him that he was the cousin of Ballon d'Or winner George Weah will never get old.

In the eloquent words of Saints legend Matthew Le Tissier: "He ran around the pitch like Bambi on ice; it was very embarrassing to watch."

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Terrible signings

Sometimes the beautiful game is beautiful for being, well, not so beautiful.

Besides, you have to wonder whether players like Dia and Gravesen were buried under a pile of four-leaf clovers and lucky rabbit's feet when they received those inexplicable phone calls.

Which reminds me... I swear I'm related to Lionel Messi, has anyone got Ralph Hasenhuttl's number?

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