Tony Pulis has been ordered to pay his former club Crystal Palace £3.7m by a High Court judge.
The West Brom manager had gone to the High Court to challenge a decision by a Premier League Managers' Arbitration Tribunal to pay Palace damages after his departure in August 2014.
The dispute centred on the payment of a £2m bonus for keeping Palace in the Premier League and remaining employed by the club until 31 August 2014.
Pulis contended that the original verdict was unfair but Judge Sir Michael Burton has upheld it.
He said: "I enforce the award and the final award both as to the liquidated damages for £1.5m in respect of the repudiation, and also in respect of the £2.276m damages for deceit plus the interest and costs awarded."
Sir Michael Burton said the tribunal had analysed evidence after Palace bosses complained about the way Pulis had left the club at the start of the 2014-15 season.
He said Pulis had a contract which would see him get the £2m bonus if he kept Palace in the Premier League in 2013-14 and stayed in the manager's job until 31 August 2014.
Pulis had kept Palace in the top flight but had not stayed until 31 August 2014.
Palace bosses had complained that Pulis had deceived them into paying the bonus early by saying he was "committed" to the club and "urgently needed the money early" so that he could buy some land for his children.
Sir Michael said Palace bosses had agreed to Pulis' request for early payment and handed over the £2m on 12 August 2014.
He said that on 13 August, Pulis told bosses he wanted to leave, and on 14 August he left.
Pulis had denied "fraud" and said he only wanted to leave if it was "mutually agreeable for him to leave on the eve of the new season", and that it had been "mutually agreeable".
Arbitrators had concluded that Pulis made "false representations". They decided he had not been "committed to the club", had not intended to stay until 31 August and "there was no such land transaction".
They also concluded that he had not told the truth and "deliberately misled" Palace chairman Steve Parish "concerning his intentions".
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