Steven Pienaar (Everton to Tottenham)
A top player during his time at Everton, Steven Pienaar looked like a smart signing by Tottenham back in January 2011.
Unfortunately, the South African attacking midfielder was a shadow of his usual self at Spurs, and lasted just a few months before heading back to Everton.
Upon returning to Goodison Park, Pienaar looked pretty good again, so Tottenham will undoubtedly feel very hard done by with this one.
Christopher Samba (Anzhi Makhachkala to QPR)
A towering and commanding centre-back for Blackburn Rovers for a number of years, Christopher Samba was often linked with bigger clubs, though those moves never materialised.
Eventually, Samba was one of a number of big-name signings by QPR as they attempted to put together a squad capable of challenging for the top four.
Like so may of those signings, however, Samba majorly flopped at Loftus Road as the London outfit ended up getting relegated instead.
Kostas Mitroglou (Olympiacos to Fulham)
Fighting relegation in 2013/14, Fulham really needed some inspiration that January, and looked like they’d secured a real coup by bringing in Kostas Mitroglou.
The Greek striker had been superbly prolific at Olympiacos, but he totally flopped at Fulham, making just three appearances and failing to score a single goal.
Mitroglou later revived his career again, but clearly the Premier League just wasn’t for him.