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There are hundreds to pick from but we think you'll all agree that these eight were very strange indeed.
Here they are in no particular order.
Julien Faubert - West Ham to Real Madrid
This one was truly bizarre.
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Why, just why!?
Faubert had struggled badly with West Ham, failing to score a goal in his first two seasons with the club.
However, Real Madrid thought they saw something everyone else didn't.
Faubert signed on a six-month loan deal and......surprise....he struggled at the Bernabeu.
He made only two La Liga appearances during his time in Madrid.
Robinho - Real Madrid to Manchester City
There'd be nothing weird about this move now.
However, Manchester City were a mid-table side when they pulled off a massive coup on deadline day.
It just happened to be the same day their new owners took over in the summer of 2008.
Robinho was on the verge of signing for Chelsea before City pulled off a huge shock.
It never really worked out for Robinho and he subsequently admitted thinking he was signing for United.
However, it can be seen as the start of a new era for City and English football as a whole.
Nicklas Bendtner - Arsenal to Juventus
Lord Bendtner once described himself as one of the world's best players and if this were true, Juventus would have pulled off a great loan move here.
In reality though, it was bonkers.
The Dane made only a handful of appearances during a season-long loan in Italy.
The club even revealed they were yet to sell a jersey with his name on it after seven months.
Allan Simonsen - Barcelona to Charlton
This will only be familiar to fans of a certain age but it ranks right up there in any list of weird transfers.
After scoring the winner in the Cup Winners' Cup final and leading Barcelona to a 2-1 win over Standard Leige, Simonsen was seen as expendable after the club signed Diego Maradona.
The 1977 Ballon d'Or winner had offers on the table from Tottenham and Real Madrid.
However, he opted to join Second Division Charlton Athletic in a £300,000 deal instead.
The Danish striker scored nine times in 13 games before returning to Denmark in a move to his first club, Vejle BK.
Kevin Keegan - Hamburg to Southampton
Hamburg had just won the Bundesliga and made the European Cup final, losing out to Brian Clough's Nottingham Forest, and Keegan had won back-t0-back Ballon d'Ors.
He could have walked into any side in Europe but he went for Southampton.
It'd be a bit like current Ballon d'Or holder Luka Modric agreeing to a surprise move to Brighton.
Bebe - Vitoria De Guimaraes to Manchester United
Alex Ferguson was responsible for bringing the likes of Cristiano Ronaldo, Roy Keane, Wayne Rooney, Eric Cantona and Nemanja Vidic to United.
However, he had his fair share of duds too. Bebe was most certainly one of them.
Ferguson agreed to pay £7 million for the Portuguese striker without seeing him play after reports that Real Madrid were looking to swoop in.
Bebe's pace was stunning but it quickly became apparent that he didn't have the technical qualities to succeed at the top level.
He's currently plying his trade with Rayo Vallecano in La Liga.
After United, he featured for the likes of Cordoba, Eibar, Pacos de Ferreira and Rio Ave.
Carlos Tevez & Javier Mascherano - Corinthians to West Ham
This double move was just about as dodgy as they come.
West Ham eventually had to fork out £5.5 million in fines for breaching Premier League rules for signing players from third-party owners.
Tevez and Mascherano played for Brazilian side Corinthians but they 'belonged' to companies owned by Kia Joorabchian.
Edgar Davids - Barnet
Davids had been without a club since leaving Crystal Palace in 2010 and most fans presumed he had retired.
In a move that came out of the blue, Davids was named as the player-manager of League Two side Barnet in 2012.
Things started well as he helped Barnet off the foot of the table but disciplinary problems plagued Davids as they had throughout his career.
He was also criticised for the bizarre decision not to attend away games that required an overnight stay.
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