The most regrettable transfers in Premier League history

It’s the January window, which means plenty of players are going to trade hands. Some clubs will end up paying far too much money for their new blood (Manchester City have already got the ball rolling on that one), while others will land a player who proves to be a bargain and a regrettable loss for their former employer. A classic example of the latter is Denis Law: Manchester United decided to let their second highest goal scorer of all time leave on a free to rivals City. Law only spent one year at City in his second spell before retiring, but his last goal came in the last game of the 1973-74 season against United. The red side of Manchester needed a win to stay up, but a Law back heel in a 1-0 win confirmed their place in the Second Division for the next season.

With this case study in mind, here’s the Premier League ‘Shouldn’t have let him go XI’…

Brad Friedel (Liverpool to Blackburn, 2000, free)
Friedel only managed 30 starts for Liverpool in three years before he was allowed to move on a free to Blackburn, after failing to displace Sander Westerveld. Since leaving Merseyside, Friedel has been one of the most consistent keepers in the league, while Liverpool have been through Westerveld, Dudek, Chris Kirkland, Pegguy Arphexad and Scott Carson, before settling with current shot stopper Pepe Reina.

Steve Finnan (Fulham to Liverpool, 2003, £3.5m)
Finnan was a key figure in the Cottagers side that won the Second Division and First Division and was a member of the PFA Team of the Year in his first season in the Premiership with them. He managed over 200 appearances for Fulham before moving to Liverpool and winning the League Cup, FA Cup and Champions League in his 5 years on Merseyside.

Jonathan Woodgate (Leeds to Newcastle, 2003, £9m)
In January 2001, Leeds were top of the Premiership. Two years later, they found themselves fighting a relegation battle. Then came the sales of Lee Bowyer, Robbie Fowler and their best defender, Woodgate - unsurprisingly their poor form continued. The following season Woodgate’s value to the team was all too evident when Roque Junior was brought in to fill the gap. Junior looked like he had money on a Leeds relegation as the club conceded 25 goals in the 7 games he played in.

Matthew Upson (Arsenal to Birmingham, 2003, £1m)
Upson only managed 20 league starts in nearly six years at Arsenal before he was sold for half the price they had previously paid for him. He excelled at Birmingam before a £6 million switch to West Ham, where his performances have been rewarded by a call up to the England team. Recent reports have suggested that following the uncertainty of the future of ex-captain William Gallas, Professor Wenger is keen to spend over £10m on bringing him back to Arsenal. If he does rejoin the club, maybe he’d have more luck starting if he changed his name to Mathieu Upsoné.

David Unsworth (Sheffield United to Wigan, 2007, free)
Mr Unsworth wasn’t the biggest success at Wigan - he only managed 10 games for the club. He did, however, manage to score the winning goal with a penalty in Wigan’s last game of the season to keep them in the Premier League. And the side who went down at Wigan’s expense? Sheffield United.