$Apple (AAPL.US)$The loss of a lawsuit involving 13 billion euros ($14.4 billion) Irish tax bill further fueled the EU's crackdown on countries providing special concessions to large companies.

The European Court of Justice in Luxembourg upheld a landmark 2016 ruling that Ireland violated state aid laws and gave Apple an unfair advantage.

The court ruled on Tuesday that Apple's victory in a lower court should be overturned because the judge wrongly determined that the Commission's regulators made a mistake in the assessment.

The ruling is encouraging for EU antitrust commissioner Margrethe Vestager, whose term in Brussels will end after two terms.

In 2016, Vestager pointed the finger at Apple's tax arrangement, which sparked anger on the other side of the Atlantic. She alleges that Ireland provided this company with illegal benefits, making it pay far less in taxes than other businesses in the country over the years.

She ordered Ireland to take back 13 billion euros, which is equivalent to two-quarters of Apple's global Mac sales. The money has been kept in an escrow account awaiting a final ruling.

An Apple spokesperson said, “We are disappointed with today's ruling because the ordinary court previously reviewed the facts and clearly declared the case null and void.”

Before the US stock market on Tuesday, Apple's stock price fell about 1% as of press release.

While this is a negative outcome for Ireland, given the time it takes to complete the case, it's unlikely to have much of an impact on Ireland, which is a mature center for the European headquarters of many of the big tech companies. Ireland has claimed that it does not provide any tax benefits for Apple or other technology companies to set up companies in Ireland.

Apple CEO Cook previously criticized the EU's move as “pure political nonsense.” The US Treasury also expressed its opinion that the EU is establishing itself as a “supranational tax authority,” which may threaten global tax reform efforts. Then-President Trump said Vestager “hates America” because “she is suing all of our companies.”

So far, the ruling in the Apple case is the largest in Vestager's decade-long tax fairness campaign, which also targets companies such as Amazon (AMZN.US) and Fiat under the automobile manufacturer Stellantis NV (STLA.US). Vestager believes that selective tax benefits for large companies are illegal state aid prohibited by the European Union.

The contentious points in Tuesday's case were two tax agreements with the Irish government in 1991 and 2007. According to the EU's assessment, these agreements allow Apple to falsely attribute Irish profits to a “headquarters” that “only exists on paper.” This, in turn, has led to a significant reduction in taxes. The EU antitrust department argues that the subsidies Apple received were anti-competitive and amounted to illegal state aid.

In 2020, after Vestager challenged Apple's victory in a lower court, the case was brought before the EU Supreme Court. The EU General Court judge found that the EU State Aid Supervisory Authority had made several mistakes.

Since then, Vestager has had several more failures in this operation, but she is pleased that the judges have supported her use of state aid rules to combat unfair arrangements.

Apple was one of the first American tech giants to set up companies in Ireland because Ireland deliberately lowered corporate tax rates in the 1980s and early 90s to attract foreign investment. The company established its European headquarters in 1980 in the southern city of Cork and currently has around 6,000 employees in the country.

In the years since then, many existing tax loopholes have been closed, and Ireland signed the OECD measures in 2021, including a 15% minimum global tax rate for multinational companies.

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