Leeds United was entitled to fire a senior executive for using the club's email to send "obscene and pornographic" images of naked women, a judge has ruled.
Gwyn Williams who was summarily dismissed for gross misconduct in July 2013, had asked the High Court to award him up to £250,000 in compensation for breach of contract.
Williams, who joined Leeds in August 2006 as technical director with an annual salary of £200,000 plus benefits, said that the email was part of a "dirty Leeds" joke, referring to the club's reputation for heavy tackling in the 1970s.
He agreed that his conduct was inappropriate after sending the email to former Chelsea colleague Dennis Wise, Gus Poyet - now Sunderland's head coach - and receptionist Carol Lamb, but argued it was not sufficiently serious to lead to a repudiatory breach of contract.
Williams told Mr Justice Lewis that the email was discovered five years and eight months after it was sent, allegedly during a forensic examination conducted to find a reason to justify not paying him his notice.
The judge said that, taken as a whole, the images in the March 2008 email were "obscene and pornographic" and not common in professional football at the time.
The photographs do more than than depict a group of muddy women showering. They involve displays of female genitalia and breasts and scenes of simulated sexual activity between women.
Mr Justice Lewis said that In his judgment, the forwarding of the email amounted to a sufficiently serious breach of the implied duty of mutual trust and confidence as to entitle the club to dismiss Williams without notice.
The sending of the images to a junior female employee might well have caused offence and left the club vulnerable to a claim for sexual harassment, he added.
Williams was refused permission to appeal although he can renew his application directly to the Court of Appeal.
He was ordered to make a payment to the club of £45,000 on account of legal costs.
Williams' lawyers said he would be pursuing a claim for unfair dismissal at an employment tribunal.