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#3 Zoran Torsic (2009-2010)
Zoran Tosic had one of the shortest spells of any player in a Manchester United jersey. After scoring 42 goals and providing 25 assists in 142 appearances at Partizan Belgrade, Sir Alex Ferguson brought the Serbian international to England in January of 2009.
However, the Scottish manager never made the youngster into his plans. Manchester United had a wealth of talent on the wings, with Anderson, Nani and Ryan Giggs hogging a major share of the minutes.
This limited Tosic to just two appearances in the 2009-10 season. In the following campaign, the Serbian was sent on loan to FC Koln before joining CSKA Moscow permanently in 2011.
Tosic went on to achieve success in Russia. However, there was never any regret among the Old Trafford faithful about offloading the winger.
#2 Manucho (2007-2009)
Mateus Alberto Contreiras Goncalves, or 'Manucho', is one of the few players to have signed for Manchester United after impressing on a three-week trial for the club. However, like Dong Fangzhuo, he faced issues over a work permit.
This led to the Angola international ace signing for Greek club Panathinaikos for the remainder of the 2007-08 season. Manucho was recalled for the 2008-09 season after he obtained a work permit.
Like many youngsters at Manchester United, the African star was also expected to develop and turn into the next superstar on the block.
However, this turned out to be tougher than expected as he was only afforded substitute appearances. Manucho never matched up to the quality of players like Carlos Tevez, Wayne Rooney, Louis Saha, Dimitar Berbatov or even a young Danny Welbeck.
He understandably sealed a loan move to Hull City for the second half of the 2008-09 campaign, following which, he permanently joined Spanish side Real Valladolid.
Manucho retired in 2019. However, he is still considered a striker who could have turned into a world-beater but failed to grab hold of his opportunities. Ferguson rarely attempted to sign youngsters in January following the Angolan's failed move to Manchester United.
#1 Alexis Sanchez (2018-2020)
Alexis Sanchez is arguably the greatest financial January transfer failure in the history of Manchester United. The Chilean was sensational in his three-and-a-half seasons at Arsenal as he scored 80 goals and 45 assists in 166 appearances. However, Sanchez failed to win the Premier League title at the Emirates.
The Chilean moved to the red half of Manchester in January of 2018 in a swap deal that involved Henrikh Mkhitaryan going the other way. On joining the 13-time Premier League champions, Sanchez stated that he was keen on proving his worth to the club.
However, it all turned sour very quickly. Arsene Wenger always promoted an attacking brand of football but United manager Jose Mourinho was never going adopt those methods. In his first one-and-a-half seasons at Old Trafford, Sanchez managed to make 45 appearances but could only score five goals in that period.
The arrival of Ole Gunnar Solskjaer hardly changed anything, with players like Jesse Lingard and Anthony Martial often given the nod ahead of the Chilean. It did not help that the South American ace was no longer the pacy winger he was due to several injuries.
Manchester United eventually sent Sanchez to Inter Milan on a season-long loan deal in the summer of 2019. The following year, he sealed a permanent move to the Italian club on a free transfer, making him a massive financial loss for the Red Devils.
After all, this was a player on massive wages and somebody that was expected to propel them to their first league title since 2013.
The January transfer window is the most tricky time of the year to conclude transfer dealings. Manchester United often bagged the best players. However, this quintet are a reminder of the dangers of dipping into the winter transfer market.
