1 Mike Tyson
Tyson is no stranger to the American judicial system as both plaintiff and defendant. In a $100m suit filed in the New York District Court in 1998, he claimed promoter Don King had cheated him out of what was rightfully his from 1995 to his ear-biting assault on Evander Holyfield in 1997. Just for good measure, he sued former managers Rory Holloway and John Horne for signing the deal that made King his exclusive promoter. Last year Tyson accepted a measly $14m, but only after the approval of the bankruptcy court, for the walking tragedy had long since squandered his $300m fortune and was as financially incapable as he would prove to be in the ring against Danny Williams a few weeks later. Much of that fortune had gone on legal fees.

2 Jean-Marc Bosman
In 1990 Bosman was an average midfielder whose contract had expired at nondescript Belgian club RC Liege. They offered him a new deal, but reduced his wages by 60%. Bosman demanded a transfer and French club US Dunkerque said “oui” if he was a free transfer. Liege refused to release him unless Dunkerque paid a fee. Career on the rocks, Bosman sued, citing freedom of labour rights within the EU. A Belgian court found for him. In 1995, after numerous appeals, the original decision was upheld by the European Court of Justice and out-of-contract players were given the right to change clubs without money changing hands.

3 Terry Venables
Owner Alan Sugar would look after the finances and Terry Venables would oversee the playing side. It should have been the partnership to take Spurs into football’s new era of plenty. Yet, in May 1993, Sugar dismissed Venables, who was promptly reinstated by the High Court for the duration of the case he instigated.

Sugar turned the tables in court and Venables moved on, but that was far from the end for El Tel’s “legal” career, and over the next few years his lawyers were busy men.

4 Kieren Fallon
Trouble has followed Kieren Fallon around like a naughty puppy and the controversies have sometimes obscured his brilliance. Even so, when The Sporting Life accused him of preventing Top Cees winning the 1995 Swaffham handicap at Newmarket, Fallon (and Lynda and Jack Ramsden, the horse’s trainers) sued for libel, claiming that while he might have made a tactical error, he hadn’t stopped the horse. Television presenter Derek Thompson claimed Fallon had told him that Jack Ramsden had given an order to pull Top Cees. The jury didn’t believe him. The Sporting Life were ordered to pay Fallon £70,000 and the Ramsdens £125,000, plus costs.

5 Ian Botham and Allan Lamb
Not men to take a perceived insult lying down, Ian Botham and Allan Lamb took offence at an interview given by Imran Khan to India Today in 1994 in which he appeared to allege that the pair were “racist, ill-educated and lacking in class”. Imran claimed he was mis-quoted and offered to write to The Times to say so publicly. Botham and Lamb declined the offer. Against a backdrop of ball-tampering allegations, they pursued the case against Khan to its bitter end. They lost. Botham’s estimated legal bill was £260,000, Lamb’s £140,000.

6 Michael Watson
Paralysed down his left side and in need of medical attention for the rest of his life after his WBO super- middleweight title fight with Chris Eubank in 1991, Michael Watson sued the British Boxing Board of Control for up to £3m. He had waited 28 minutes for resuscitation after collapsing at the end of the fight. In 1999 Judge Ian Kennedy upheld Watson’s claim, decreeing that the delay had contributed to his irreversible brain damage and was beyond normal boxing risks. The ruling enshrined the principle that sports administrators were responsible for participants’ well-being.

7 Gordon Watson
In 1997 the career of Bradford City’s then-record signing Gordon Watson wasn’t quite ended by a savage tackle from Huddersfield Town’s Kevin Gray. Even so, “Flash” was out of the game for 18 months after his leg was broken in two places and was never the same player again. The court decided that Gray knew on balance that there was a chance he would cause injury with his near-horizontal assault. Therefore Watson was awarded £909,143 in damages and Gray found himself responsible for football’s most expensive tackle.

8 Paul Elliott
In September 1992 the career of Chelsea defender Paul Elliott was finished after a tackle from Liverpool’s Dean Saunders at Anfield. Elliott sued Saunders, claiming the tackle was reckless and that the Welsh striker had dived in with his feet up. After lengthy proceedings, the judge accepted that although Saunders did go in with those feet up, the seemingly offensive posture was in fact a defensive measure in the heat of the moment to avoid injury himself. Thus Saunders’ actions were not in breach of his duty of care to Elliott. Elliott thus found himself ruined, financially and professionally

9 Tony Greig, John Snow and Mike Procter
In 1977 the International Cricket Conference (ICC) and the Test and County Cricket Board (TCCB) decreed that any player who had signed for Kerry Packer’s World Series would be banned from Test cricket, in effect ending the England careers of Greig and Snow. With Packer’s help, they and South African player Mike Procter took the case to a London court. Judge Slade agreed that the World Series was a destructive force in cricket, but as the ICC and TCCB did not have a contractual relationship with the players and Packer did, Slade had no choice but to find for the players.

10 Tommy Docherty
Disgruntled at being dropped by Tommy Docherty while a Manchester United player in 1975, a couple of years later Willie Morgan announced on television that Docherty was “about the worst manager there’s ever been and nearly all United fans will be glad when he goes”. Docherty sued Morgan for libel. Morgan put his life on hold to fight the case and recruited several former teammates to speak on his behalf. Under cross-examination, Docherty admitted he had told “a pack of lies”. Later he was tried (and acquitted) on perjury charges. “Bringing the case,” said a chastened Doc, “was the worst mistake of my life.”