AC Milan forward Rafael Leao has been ordered to pay former club Sporting Lisbon €16.5million (£13.8m), according to reports in his native Portugal.
The 22-year-old is said to have lost an appeal over a contract dispute dating back to June 2018.
Leao decided to terminate his deal with Sporting after roughly 50 of the club's fans, some of whom were armed, broke into the training ground and attacked their own players.
He would go on to join Lille in August that year before signing for AC Milan in the summer of 2019.
However, Sporting filed a complaint with FIFA over his move to Lille and claimed they were owed his €45million (£37.7m) release clause.
In March 2020, the Court of Arbitration for Sport (CAS) ordered Leao to pay £13.8million to Sporting because of his unilateral breach of contract.
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CAS deemed a sum in the region of €15million (£12.6m) and €18million (£15.1m) was fair compensation for the Portuguese giants, as opposed to the full value of his release clause.
Leao sought to have the decision annulled through the Lisbon Court of Appeal, but Portuguese outlet Record, per Calcio e Finanza, claims he has been unsuccessful in his efforts.
This means he must pay the fee to Sporting or take his appeal to the Portuguese Supreme Court.
The Court of Appeal's verdict is crushing news for a player who has caught the eye in Italy this season.
Leao has eight goals and five assists in 24 appearances, and he earned his first senior caps for Portugal in late 2021.
Generally deployed as a left-winger, he has two-and-a-half years remaining on his contract at San Siro and has relished his development under manager Stefano Pioli.
Speaking last week, Leao said: "Pioli understands me, he knows that with my dribbles and my moves I can make a difference.
"Before, he took great care with me in the tactical aspect, I was younger and more undisciplined. Now he doesn't explain much to me, he trusts me, he knows that I do my part even when the opponents have the ball."
Leao even claims his manager has compared him to former Arsenal and Barcelona superstar Thierry Henry.
"He (Pioli) tells me, 'Stay wide and challenge your man'," he added. "For me, everything becomes easier. I have also played as centre-forward and as a 10, I'm ready to do it again if needed, but on the left is another thing.
"Pioli thinks I'm like Henry? I thank him for the comparison, we are talking about a great champion, but I want to be Rafa, I want to go my own way."
