1 Ben Davies/Michel Vorm - Gylfi Sigurdsson
Ben Davies/Michel Vorm: Swansea City
Gylfi Sigurdsson: Tottenham
Starting off with a transfer that involved Spurs themselves, this was a cleverly engineered deal from Daniel Levy that included two Swansea players for the price of one.
Gylfi Sigurdsson was on the fringes of the Tottenham team, with Swansea desperate for the Icelandic international to return to the club, this time permanently after a previously successful loan spell in Wales.
Spurs themselves were in need of a backup goalkeeper and a rotation option for Danny Rose at left back.
The transfer worked out for all parties, with Davies and Vorm proving excellent squad players and Sigurdsson showing how good he can be, eventually resulting in a £45m transfer to Everton this summer.
2 Samuel Eto'o + £40m - Zlatan Ibrahimovic
Samuel Eto'o: Barcelona
Zlatan Ibrahimovic: Inter Milan
This is yet another example in a long list of bizarre Barcelona transfers. Samuel Eto'o had formed a frightening attacking partnership with Thierry Henry and Lionel Messi at the Catalan club which helped them to the treble in Pep Guardiola's first season in charge.
Their rotation and fluidity was key to the partnership, allowing Messi to play as the false nine. However, the signing of Ibrahimovic forced Barcelona to change their style, as the Swedish international took the central position.
Despite winning the league and being recognised as one of the greatest strikers ever, the transfer didn't work out for Barcelona and he left after a year after he was forced to play out wide.
Eto'o, on the other hand, was sensational for Inter Milan, helping the side to win their first, and his second ever treble.
3 William Gallas + £5m - Ashley Cole
William Gallas: Chelsea
Ashley Cole: Arsenal
Recognised as the best left back in Europe, Jose Mourinho was desperate to add the England international to Chelsea's ranks.
It was deemed as one of the most controversial moves in transfer history, with Mourinho, Chelsea, and Cole himself found guilty of going behind Arsenal's backs to discuss the transfer in 2005.
Chelsea were consequently fined for tapping up in 2006.
William Gallas was largely a success at Arsenal, though he eventually left to join arch-rivals Tottenham. Cole, however, won everything there was to win at Chelsea.
4 Jose Antonio Reyes - Julio Baptista
Jose Antonio Reyes: Arsenal
Julio Baptista: Real Madrid
Neither was a major success in their respective stints at each club and it led to a rather bizarre transfer deal.
In fairness, Reyes played some part in helping Real Madrid to a La Liga title, but Baptista showed his quality in fits and spurts, particularly in the League Cup where he helped Arsenal reach the final, losing to Chelsea.
After their loan deals had ended, Reyes joined Atletico Madrid permanently, whilst Baptista left for Italian side Roma.
5 Antonio Nunez £8m - Michael Owen
Antonio Nunez: Real Madrid
Michael Owen: Liverpool
Owen had won the Ballon d'Or in 2001 and was signed as part of a new wave of Galacticos by Real Madrid in 2004.
However, despite largely impressive when given a chance, Owen failed to hold down a regular spot at the Spanish giants, being sold only a year later to Newcastle United.
Nunez failed to live up to any of his hype for Liverpool. This is a transfer deal both clubs would have second thoughts about doing if given another chance. Hindsight is a wonderful thing!
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