Paris Saint-Germain must pay €10 million ($10 million) for breaking UEFA financial rules, with seven other clubs also punished for overspending since 2018.
UEFA said its club finance investigators ordered prize money from European competitions totaling €26m ($26.1 million) to be withheld from the eight clubs sanctioned under Financial Fair Play rules.
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A further €146m ($146.4m) in total punishments could be imposed if the clubs fail to meet financial targets in the next three to four years they have agreed to in settlement deals, UEFA said.
PSG will have the biggest amount deducted with a group of Italian clubs next in line: AS Roma must forfeit prize money of €5m ($5m), Inter Milan €4m ($4m), Juventus €3.5m ($3.5m) and AC Milan €2m ($2m).
French champion PSG declined to comment on the case, which covered the 2021-22 season when it added Lionel Messi to a super forward line that already featured Kylian Mbappe and Neymar.
AC Milan said in a statement, "We will continue with confidence on the virtuous path towards financial sustainability." The Italian champion was bought this week by American investors RedBird Capital Partners in a €1.2 billion deal that included the New York Yankees as a minority partner.
The other deductions imposed were €600,000 from Besiktas and €300,000 each from Marseille and AS Monaco.
The sanctions covering the financial years from 2018-22 -- including two seasons when club revenue was severely hit by the COVID-19 pandemic -- should be the last major round of cases under the FFP rules that UEFA announced in April will now be modified.
UEFA launched FFP a decade ago to monitor the revenue and spending of clubs that qualify to play in its club competitions to ensure they approach break-even on their football-related business.
Clubs were allowed unlimited spending on stadium and youth development projects.
Qatar-backed PSG had to pay UEFA €20 million in 2014, when Abu Dhabi-owned Manchester City had to pay the same amount, in the first round of FFP cases.
Man City were among 19 clubs named who met the break-even standard only on technicalities, UEFA said, such as concessions made for the pandemic seasons when many games were played without fans. Other clubs in this category were Barcelona, Borussia Dortmund, Chelsea, Sevilla and West Ham.
Among other cases, Champions League team Porto were threatened with a one-season ban from UEFA competitions if it failed to meet a new break-even target.
The cases were investigated by a panel whose new chairman is Sunil Gulati, the former United States soccer federation president and FIFA executive committee member who is an economics lecturer at Columbia University.