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#3 Martin Demichelis | Malaga - Atletico Madrid - Manchester City (2013)
Martin Demichelis had an unforgettable transfer window in 2014. The Argentine centre-back enjoyed three good years at Malaga, taking them from near relegation to the Champions League during his time at the club. He later ended up leaving the club on a free transfer to Atletico Madrid.
However, just two months into his time in the Spanish capital, former Malaga boss Manuel Pellegrini lured the defender to Manchester City. The Premier League giants ended up paying €4.5 million for Demichelis, who Atleti signed on a free transfer just a few weeks back.
Demichelis had a successful first season at City, helping them win the Premier League title in 2014. He spent another two seasons at the club before moving to Espanyol in 2016. He eventually returned to Malaga just six months later.
The 40-year-old is currently the manager of Bayern Munich's second team.
#2 Bebe | Estrela - Vitoria di Guimaraes - Manchester United (2010)
Sir Alex Ferguson did not make many bad signings during his time at Old Trafford. But the transfer of unknown Portuguese winger Bebe was definitely one of them.
Bebe came to prominence in 2009 when he joined Portuguese third-tier side Estrela and became the club's star man during that season. His performance saw top-flight side Vitoria swoop in to pick up the youngster on a free transfer in July 2010.
Following a brilliant pre-season in which he scored five goals in six matches, Bebe's buy-out clause was increased from €3 million to €9 million.
After just five weeks with Vitoria, Manchester United activated that release clause to seal the transfer of the Portuguese youngster. There was even talk of Bebe being the next Cristiano Ronaldo.
That was not the case, however, as Bebe failed to live up to expectations at Old Trafford. He was handed a few first-team chances by Ferguson but ended his first season with just two goals in seven appearances.
Bebe never donned United's red again, heading back to Portugal on several loan deals before sealing a transfer to Benfica in 2014.
Now 31, Bebe currently plies his trade at Rayo Vallecano in the Spanish top-flight after helping them achieve promotion from the second-tier last season.
#1 Dietmar Hamann | Liverpool - Bolton - Manchester City (2006)
Liverpool legend Dietmar Hamann is arguably the most high-profile example of a player who moved twice in the same transfer window.
Hamann endured some of the best years of his career at Anfield. The German midfielder spent seven seasons on Merseyside and was part of Liverpool's memorable Champions League win in Istanbul. He came on at half-time when the Reds were 3-0 down and helped them make a miraculous comeback to draw the game 3-3 and win on penalties.
But a year later Hamann left Liverpool on a free transfer and signed a pre-contract with Bolton Wanderers in June. The German midfielder linked up with his club on July 11 but suddenly had a change of heart when Manchester City expressed interest in signing him.
Bolton allowed Hamann to join the Citizens and pocketed €600,000 from his transfer.
Hamann's decision appeared to be the wrong one as Bolton managed to finish seventh that season, earning them a UEFA Cup spot. City, on the other hand, ended the season in 14th place.
Hamann spent three seasons at the Etihad before ending his career at League One side MK Dons in 2011. He now works predominantly as a pundit and football writer.
