OTP revisits some of the transfers that the country’s largest clubs would rather forget…



10. Robert Fleck

Fleck is one of those strange players that almost become legendary with a club’s fans for being poor (in the fashion of Jason Lee). Chelsea fans still sing to the tune of Yellow Submarine about the Scottish striker. He joined the club just before the Premier League began for a club record £2.1million and scored four goals in 48 appearances before being loaned out Bristol City and Bolton Wanderers.

9. Juan Veron

Manchester United can be somewhat forgiven for spending big bucks on Veron, because he was a huge success at Lazio. But after flopping at Old Trafford, Veron was a strange way for Chelsea to spend £15million . Amazingly, the Argentina international cost Chelsea more than £2million per Premier League appearance, and spent three years out on loan before finally leaving in 2007.

8. Yuri Zhirkov

Zhirkov was sold for £13million, so his poor performances in a Chelsea shirt must be put into context. The club only lost £5million on the Russian. Zhirkov’s principle problem was that he is a left-back by trade, and yet Chelsea already had the best left-back in the world at their club. Tried in other positions, including left and central midfield, Zhirkov never managed to hold down a place.

7. Gabriele Ambrosetti

Laughably bad, Ambrosetti was labelled as the Italian Giggs by Gianluca Vialli, and as far as I know he was never knocking off a member of his extended family. He never made himself a regular, and left after four years and a handful of appearances. £3.5million well spent!

6. Pierluigi Casiraghi

Possibly harsh on the Italian, given that his football career was ended just ten games after a Chelsea move, after suffering a cruciate ligament injury. However, he had scored just one goal in those ten appearances, and a £5.4million fee looked to be drastically over-the-odds.

5. Paul Furlong

An old skool one this, but Furlong became Chelsea’s record signing when he joined from Watford in the summer of 1994 for a fee of £2.3million. In fairness to the big striker, he signed in the wrong era, just before Chelsea were to sign players such as Gullit and Vialli, and he soon found himself down the pecking order. He eventually joined Birmingham City after two seasons and 13 goals.

4. Winston Bogarde

It’s impressive that Bogarde holds his place in the top five despite not even costing a fee. Even the player admitted he may have been the worst signing ever, given that he sat out the entirety of a four-year contract despite making only nine appearances, training with the youth team for the last two seasons. He then named his autobiography ‘This Negro Bows For No-one’.

3. Andriy Shevchenko

The original Torres? Sheva cost £30million when he joined Chelsea from AC Milan, and was rumoured to be an Abramovich signing rather than one that Jose Mourinho had approved. He stayed at Stamford Bridge for two seasons, plundering just 9 league goals, before re-joining Milan on loan and then moving back to his homeland with Dynamo Kiev

2. Chris Sutton

Signed by Gianluca Vialli for a massive fee of £10million, Sutton simply never looked like performing at Stamford Bridge. He scored just one goal for the club in the Premier League in 28 games, and after just one season was sold to Celtic. He would have been number one on this list, but somehow Chelsea managed to get £6million for Sutton.

1. Fernando Torres

Yes, he is still there, and yes, he looked better towards the end of last season. But Torres is still the most expensive transfer in English football history, and has still only score seven Premier League goals at Chelsea, at a rate of less than one every nine games. And when you actually think about that, it’s dreadfully poor.

Have we missed your favourite worst Chelsea signing? Let us know below.