No10: Khalid Bhoularouz

Jose Mourinho hailed Khalid the Cannibal after his £8m arrival after earning a reputation as a fearsome defender. But Bhoularouz failed to nail down a regular spot and was soon shipped out on loan to Seville. He completed a switch to Hamburg this summer for around half the fee he cost two years ago.

No9: Asier Del Horno

Another odd signing from Mourinho. Despite possessing Wayne Bridge in the pre-Ashley Cole days of 2005, the Blues paid £8m for left-back Del Horno. Yet, the Spaniard never settled at the Bridge and was flogged to Valencia at a loss of £3m just a year later.

No8: Scott Parker

Flush with Abramovichs cash at the start of 2005, Claudio Ranieri opted to splash out £10m on Parker. The midfielder emerged as a true star at Charlton but he was unable to leapfrog Frank Lampard and Claude Makelele into Chelseas team. After a frustrating 18 months, he left for Newcastle for £6.5m.

No7: Geremi

One of the first to join at the start of Abramovichs money-mad era. The midfielder may have arrived in a £7m deal from Real Madrid but he was never more than a bit-part player at the Blues. After four seasons of struggle at the Bridge, Geremi still only 28 at the time headed to Newcastle on a free.

No6: Damien Duff

Eyebrows were raised when Chelsea paid Blackburn £17m for Duff in 2003 but he initially looked good value on the opposite wing to Arjen Robben. Yet, injuries hampered the Irishmans development and, three years after his arrival, the Blues sent him to Newcastle who else? for just £5m.

No5: Shaun Wright-Phillips

Wright-Phillips was supposed to the answer to Chelseas search for a natural right winger even though there was shock at the £21m fee. Mourinho and later Avram Grant failed to find room for his talent and it was no surprise when Phil Scolari let him go. Even at a loss of £12m.

No4: Juan Veron

Even without the aid of hindsight, this was arguably Chelseas oddest buy. Veron was a huge failure at Manchester United but the Blues gave him a second chance with a £15m deal in 2003. To no-one's surprise, the midfielder again flopped and was eventually sneaked out on a free last year.

No3: Adrian Mutu

Chelsea splashed out £15.8m on Mutu in 2003 but he was sacked for taking cocaine a year later. The Blues effectively gave the striker away for free, with Juventus signing him after his seven-month suspension. However, the star has now been ordered to pay Chelsea over £13m in damages.

No2: Hernan Crespo

The Argentina ace carved out a reputation as one of the worlds deadliest strikers during his time in Italy. Crespos arrival for £16.8m in 2003 signalled Abramovichs intent. But the star failed to take England by storm and after a series of loans, he was released this summer for nothing.

No1: Andriy Shevchenko

This list has featured a string of huge losses but none of them come close to the Shevchenko saga. Signed for a British record £30m in 2006, the striker became arguably the biggest flop in the game's history. After two painful years, Sheva was gone for a tiny fraction of his whopping fee. Shocking business.