Highlights

  • After months of searching for a new club, Jesse Lingard's transfer to FC Seoul shocked the footballing world.
  • Carlos Tevez and Javier Mascherano's move to West Ham remains one of the biggest transfer surprises in Premier League history.
  • Gennaro Gattuso was initially reluctant to accept the offer to join Rangers, but his father convinced him by emphasising the significant amount of money involved.

The transfer window is a time when clubs scour the globe in an attempt to find the next big thing and help improve their team. Examples like Cristiano Ronaldo's move to Real Madrid and Thierry Henry's move to Arsenal will go down as two of the greatest transfers in the history of the game.

While a lot of transfers have proven to pay dividends, there have been a few examples over the years that have shocked the world. Many will remember Carlos Tevez and Javier Mascherano's move to West Ham in 2006 as well as Jay Jay Okocha's switch to Bolton.

There are some examples that have been so bizarre, that the players' agent deserves a pay rise for managing to secure their client a sensational move, with the most famous transfer that springs to mind is Julien Faulbert's move to Real Madrid from Premier League side West Ham. WIth fans witnessing many strange signings over the years, who else makes the cut?

1 Jesse Lingard to FC Seoul

One of the most bizarre transfers in football history

Jesse Lingard

After falling out of favour with Manchester United, Lingard was linked with a number of Premier League clubs in 2022. While West Ham and Newcastle were desperate to secure his signature. However, Nottingham Forest managed to tie him down for a reported £200,000 a week. The transfer shocked the footballing world, with some fans wondering how they could afford his wages.

A year later, he was released after a dismal spell. If you think his transfer to Forest was an odd one, he made an ever stranger move in 2024 when he joined South Korean side FC Seoul on a two-year deal, becoming the highest-profile foreign player ever signed by a K League club. Lingard will be hoping to get his career back on track while out in Asia.

2 Carlos Tevez and Javier Mascherano to West Ham

One of the biggest transfer shocks in the league

Carlos Tevez and Javier Mascherano sign for West Ham

To this day, nobody knows how the Hammers managed to lure two of the biggest stars that Argentina had to offer to Upton Park in 2006. In the end, the pair used the move as a pit-stop before moving on to bigger and better things in their respective careers. Tevez struggled to become a regular household name during his time in east London and fell out with Alan Pardew before Alan Curbishley's arrival in December 2006.

In the second half of the campaign, the former forward was pivotal in the Hammers' battle against relegation. He scored the only goal on the final day of the season against Manchester United to win 1-0, securing their place in the Premier League. His spell towards the back end of the season earned him a move to Old Trafford. Mascherano was like Tevez, rarely featured in his only season at Upton Park before securing a move to Liverpool the following season.

3 Gennaro Gattuso to Rangers

His father was keen for his son to make the switch

Gennaro Gattuso in action for Rangers

While Gennaro Gattuso is best remembered as an AC Milan legend, many fans may forget that he once swapped sunny Italy for Glasgow as a teenager when he moved from Perguia to Rangers. The former Italy international didn't initially want to accept the seizable offer, having not been keen on moving to Scotland.

However, after a conversation with his father, Francessco, he would go on to shake hands with manager Walter Smith and famously became a Ger. Gattuso revealed his father threatened him, saying in an interview in Spain via the Mirror.

"I didn't want to go to Glasgow. I had played two games in Serie B and was promoted to Serie A with Perugia, where I played eight games without a contract.

"Then I played the under-19 finals with Italy. One day, my father comes and tells me that a representative of Glasgow Rangers has come to town and has offered a contract to me. I didn't want to leave and I told this to my father.

"He told me that the money they were offering was so much he couldn't even write down the total figure. He told me it was four times his total earnings in his lifetime.

"When I still said no, he said he would punch me if I didn't accept it, so I signed for Rangers! I went to Glasgow and I didn't know anyone and didn't have two words in English. But after two weeks, I looked more Scottish than a Scottish player.

"I trained three or four times a day, I would go to the gym for hours. I built myself up with this mentality. I knew I didn't have great technique, but I prepared myself to mentally kill my opponent. I have dedicated my life to football."

Smith, who brought Gattuso to Glasgow, left the club in 1998. Smith's successor, Dick Advocaat, was not a fan of the Italian, with Gattuso featuring out of position before eventually being sold to Salernitana for £4 million in 1998.

4 Juninho to Middlesbrough

Many top European teams were keen on his signature

Juninho signs for Middlesbrough

After a successful spell in Brazil with Sao Paulo, many European clubs were chomping at the bit to sign Juninho. However, the Brazilian somehow miraculously ended up in north Yorkshire with Middlesbrough and managed to attract him three times to the club during his career.

Juninho was signed for £4.75 million, just months after the club had been promoted to the Premier League. During his time, he became known as "TLF" (The Little Fella) by Boro fans. After making his debut in a 1-1 draw against Leeds United in November 1995, he would go on to help the club win the League Cup in 2004 – the team’s first and only major honour.

5 Jay Jay Okocha to Bolton

Arguably one of the most skilful players ever

Jay-Jay Okocha premier league

Jay Jay Okocha will go down as one of the most skilful players to feature in the Premier League. If you search for his name on YouTube, you will not be disappointed by the results. After leaving PSG in 2002, Bolton managed to tie him down to a contract and played a key role in guiding the club away from relegation.

In the 2003/04 season, Okocha was given the captain's armband following Guðni Bergsson's retirement. As captain he led the side to the 2004 Football League Cup final, their first cup final in nine years, where they eventually lost to Middlesbrough. File Okocha in the category of players the 'streets won't forget.' Even to this day, he remains a club icon.

6 Julien Faubert to Real Madrid

It's bizarre what the Spanish giants saw in the Frenchman

Julien Faubert

After only making eight appearances for West Ham in his first season with the club, Julien Faubert somehow managed to secure a move to Real Madrid the following year. The entire football world was shocked when the Spanish giants took the player just before the close of the 2009 January transfer window.

There was an option to make the move permanent at the end of the season; however, it was never taken up by Los Blancos. Faubert didn't help his case after he missed one training session as he mistakenly thought he had the day off. His loan spell ended with just two appearances, and he would eventually return to Upton Park.

7 Joey Barton to Marseille

He was not allowed to play any league games for the first four months

Joey Barton

After playing a key role in QPR's survival season in 2011/12, Joey Barton decided to make the switch from west London to Marseille. However, he endured a tough end to the season after being sent off against Manchester City in the final game of the season for violent misconduct after elbowing Carlos Tevez in the face. He was subsequently banned for 12 matches, with the ban being upheld in French football - restricting the Englishman to Europa League football for the first four months of the season.

He made his league debut in a 1–0 home win against Lille in November 2012. In total, during his time in France, Barton made 25 appearances, helping the club finish second in the league table. His most viral moment during his spell with the club came at a press conference where his attempt at a French accent had the UK media in stitches.

8 Bojan Krkić to Stoke

He was once dubbed the next Lionel Messi

Bojan celebrates for Stoke

Having been dubbed the next Lionel Messi at one point, Bojan burst onto the scene at Barcelona in 2007 at the age of 17, breaking Messi's record of the youngest player to feature for the club in a La Liga match. After eventual spells at Roma, AC Milan and Ajax, the Spaniard made the decision to swap Tiki-taka for long-ball at Stoke City, much to the surprise of many.

Bojan signed a four-year deal with the Premier League side back in 2014, with then manager Mark Hughes saying, per the Guardian: "Anyone who knows European football will be aware of him as a player and the fact that he sees his future at Stoke City is really exciting." Believe it or not, the Spaniard stayed at the club for five seasons and even played for them in the Championship.

9 Esteban Cambiasso to Leicester City

He could've been a Premier League champion...

Esteban Cambiasso celebrating for Leicester City

After two years at Real Madrid, Esteban Cambiasso made the switch to Inter Milan, spending 10 years at the club, winning five league titles and a Champions League. After leaving Milan in 2014, at the age of 32, the Argentinian made the move to the Premier League, but surprisingly, to Leicester City.

Real Madrid - Inter Milan - Leicester City. An unconventional career path to say the least, but Cambiasso’s move to the King Power Stadium proved to be a massive hit. His first goal came in a dramatic 5-3 win against Manchester United in September 2014. He proved to be a real fan-favourite, and if he’d only stayed an extra year, he’d have a Premier League winners' medal.

10 Nicklas Bendtner to Juventus

It unfortunately didn't pay off...

Nicklas Bendtner in action for Juventus

After coming up through the ranks at Arsenal, Nicklas Bendtner was handed his first team debut in 2005. However, he was soon loaned out to Birmingham City for the 2006/07 season. He returned to north London ahead of the 2007/08 campaign. Robin van Persie was seen as the first choice striker for obvious reasons during the Dane's time with the Gunners. After a loan move to Sunderland in 2011, the former striker eventually made the switch to the Serie A a year later, signing for Juventus.

With the Italian giants having the likes of Fabio Quagliarella, Nicolas Anelka and Sebastian Giovinco in their ranks, it proved to be a bizarre signing, bringing in Bendtner. Sadly, it did not prove to be a stroke of genius as Bendtner scored no goals in Turin and was shipped back to Arsenal.

11 Luther Blissett to AC Milan

He couldn't stay away from Watford for long

Luther Blissett spotted ahead of the FA Cup final in 2019

Watford’s all-time appearances maker and top scorer, Luther Blissett will forever be hailed as a club legend by the club. After spending eight years at Vicarage Road, the former forward joined AC Milan for £1 million back in 1983. Unfortunately, it's fair to say that the Englishman endured a tough spell in Milan.

After just one season with the Serie A giants, Blissett only managed to score just five goals. The former England international re-joined his beloved Watford in 1984, going on to score 44 goals in 127 games in his second stint at the club. It's fair to say the 66-year-old didn't regret leaving sunny Milan to return home.

12 Ali Dia to Southampton

He only made one appearance

Southampton's Ali Dia.

Dubbed by many as the 'worst player in the history of the Premier League,' Ali Dia somehow managed to secure a dramatic move to Southampton in 1996. The move proved to be an absolutely sensational one after Souness was convinced that he was George Weah's cousin. To be playing in non-league football and then signing for a top team in England just days after takes some doing.

Souness gave Dia a one-month contract, even subbing the player on and then off in a Premier League match against Leeds. After a horrendous debut, the forward was eventually released just two weeks into his contract. Former Saints legend Matt Le Tissier had some harsh words to say about Dia, saying, per the Daily Star: “He ran around the pitch like Bambi on ice; it was very embarrassing to watch.''

13 Eric Maxim Choupo-Moting to PSG

His agent deserves a massive pay rise

Eric Maxim Choupo-Moting

Eric Maxim Choupo-Moting scored just five goals in his first season with Premier League side Stoke City. Somehow, it was still enough to attract the interest of European powerhouse PSG. Featuring along with the likes of Neymar and Kylian Mbappe; surprisingly, the Cameroon international managed to spend two years in France.

In 51 appearances for the Parisian side, the forward scored nine goals in 51 appearances. Despite his poor record in France, he secured a move to Bundesliga side Bayern Munich after his contract expired. Whoever his agent was, deserves a massive pay rise.

14 Christian Eriksen to Brentford

Many feared he would never play again

Christian Eriksen

In 2021, Cristian Eriksen featured in Denmark's opening group stage match against Finland in Copenhagen. Towards the end of the first half, the midfielder collapsed as he was about to receive a throw-in. It was revealed he suffered a cardiac arrest, with many wondering if he would play again. Soon after, it was announced that he was not permitted to play in the Serie A due to the presence of an implantable cardioverter-defibrillator he had implanted.

Yet six months later, Premier League side Brentford took a chance on the Dane, and he proved to be an instant star for the club. After playing a key role for the west London club that year, Manchester United decided to take a gamble on him last season and has gone on to become one of their key players.

15 Jack Wilshere to Aarhus Gymnastikforening

His career was hampered with injuries

Jack Wilshere

Jack Wilshere was an incredibly gifted player at the peak of his powers and was a joy to watch; unfortunately, injuries ruined a career that had promised special things. After leaving north London, his short spells at Bournemouth and West Ham were plagued by injuries. After he was let go but the Cherries in 2021, the former England midfielder had one last hurrah, which had a surprising twist.

In February 2022, Wilshere signed for Danish Superliga side Aarhus Gymnastikforening on an initial short-term contract until the end of the 2021/22 season. Prior to his switch to Denmark, Wilshere had been training with former club Arsenal and Serie B club Como 1907. After his short term contract came to an end in Denmark, Aarhus announced that they would not be renewing his contract.

16 Martin Braithwaite to Barcelona

He will not go down as a club legend...

Martin Braithwaite looks in disappointment

Martin Braithwaite has endured quite a bizarre career so far. After unsuccessful spells at Middlesbrough and Leganés, in 2020, Barcelona decided that they would sign the forward to play alongside Lionel Messi. Braithwaite had scored six league goals the season before joining the La Liga giants. The Spanish side became the first team to take advantage of a rule in the country which allowed them to sign a player outside of the transfer window. They did it after Ousmane Dembele was ruled out for six months, with Luis Suarez also injured. Barcelona had to prove that the Frenchman was out for six months before being allowed to make the move for the Denmark international.

Even more surprising, Barcelona triggered his $18 million (£15.3m) release clause to sign him. In 58 appearances for the club, the Dane managed to score just 10 times and eventually had his contract terminated following an unsuccessful two years at Camp Nou.

17 Bebe to Manchester United

Many are still wondering why they signed him

Bebe

After joining Vitoria de Guimaraes from Estrela on a free transfer, before even making a competitive appearance for the Portuguese outfit, Premier League giants Manchester United surprisingly managed to poach the forward for approximately £7.2 million ($9.4m) in August 2010. Even worse, Red Devils boss Sir Alex Ferguson had never even seen the forward play, admitting that he sanctioned the signing after former assistant manager Carlos Queiroz advised him to.

Two years later, it was reported that there was a Portuguese police investigation into the transfer after it emerged that football agent Jorge Mendes pocketed 40 per cent of the transfer fee. However, no charges were pressed against anyone involved. Bebe would go on to prove to be a real flop and left Old Trafford in 2014 for Benfica, after three loan moves and just two Premier League appearances. He went viral in January 2024 after scoring arguably the goal of his life with an outstanding free kick during the Africa Cup of Nations.

18 Edgar Davids to Barnet

From sunny Milan to miserable Barnet

Edgar Davids - Barnet Player Manager in the number one shirt

Edgar Davids has featured for some of the biggest clubs in the world during his glittering career. After winning a Champions League title and several Serie A titles during his time as a professional footballer, the former Holland international ended his career at Barnet. Davids left Crystal Palace in 2010 and was living in London since parting ways with the club.

After turning up at Barnet, he joined the club as a player-coach, it's fair to say that his time at the club was very eventful. He picked up several yellow and red cards during his spell with the club and even refused to attend away games that required an overnight stay, as well as wearing the number one kit for the 2013/14 campaign.

19 Ben Davies to Liverpool

He would go on to fail to make an impact

Ben Davies in action for Preston North End

Over the years, we have seen several players move from the Championship to the Premier League. While it's mainly young stars who make the big step-up, many were surprised to see Ben Davies move to Liverpool in 2021. Having made well over 100 appearances for Preston North End, the defender joined the Merseyside outfit. While many were shocked to see him join the club, it made sense. Jurgen Klopp's side had so many major injury problems, with both Virgil van Dijk and Joe Gomez out for the season, and Fabinho having to play a few games in defence. Unfortunately, despite the injury problems at Liverpool, Davies failed to play a single minute for the first team.

After failing to make an impact, Davies joined newly relegated Sheffield United ahead of the 2021/22 season, where he would go on to become a regular for the Blades. The defender secured crucial minutes under his belt during his time up north; however, he failed to get into Klopp's side and was sold to Rangers in the summer of 2022.