LONDON >> The European Union’s highest court Tuesday delivered the 27-nation bloc a major victory in its yearslong campaign to regulate the technology industry, ruling against Apple and Google in two landmark legal cases.

The decisions, issued by the Court of Justice of the European Union, were seen as an important test of efforts in Europe to clamp down on the world’s largest technology companies. Apple and Google have been frequent targets for EU regulators, and the companies have battled the cases with appeals.

In the Apple case, the court sided with a European Union order from 2016 for Ireland to collect 13 billion euros, worth about $14.4 billion today, in unpaid taxes from the company. Regulators determined that Apple had struck illegal deals with the Irish government that allowed the company to pay virtually nothing in taxes on its European business in some years.

Apple won an earlier decision to strike down the order, a ruling that the European Commission, the EU’s executive branch, appealed to the Court of Justice. As the case wound its way through the appeals process, the 13 billion euros were placed in an escrow account. The money will now be released to Ireland, a sizable injection to the country’s treasury.

Apple said the decision effectively allowed the European Union to impose an additional tax on company income that is already taxed in the United States.

“This case has never been about how much tax we pay, but which government we are required to pay it to,” Apple said in a statement Tuesday. “The European Commission is trying to retroactively change the rules and ignore that, as required by international tax law, our income was already subject to taxes in the U.S.”

Apple said in a regulatory filing Tuesday that it expected to record a one-time income-tax charge of nearly $10 billion in its fourth quarter, which ends Sept. 28.

In the Google case, the court agreed with the commission’s 2017 decision to fine the company 2.4 billion euros for giving preferential treatment in Google search results to its own price-comparison shopping service over rival offerings. Google lost an appeal in 2021.

Google said in a statement Tuesday that it was “disappointed” by the ruling but that it had already adjusted its products to comply with the 2017 decision, including new designs to steer consumers to rival shopping price-comparison websites. Some competitors have complained Google’s changes have not gone far enough.

“Our approach has worked successfully for more than seven years, generating billions of clicks for more than 800 comparison shopping services,” Google said in the statement.

When the European Union penalized Apple and Google, the cases represented a major shift in how the tech industry was regulated. Until then, governments around the world had largely taken a hands-off approach to tech oversight as Apple, Google, Amazon and Facebook — now renamed Meta — ballooned in size and remade how people live, work, shop and communicate.

The cases helped establish the European Union and its antitrust chief, Margrethe Vestager, as the world’s most aggressive tech industry watchdog. Other countries have followed Europe’s lead to intensify scrutiny of the sector’s business practices, particularly in the United States.

Yet years later, the cases have also come to represent the grinding pace of the EU regulatory system and have raised broader questions about whether authorities can keep up with the rapidly evolving tech sector.

The two cases address different legal issues. The Google case is largely about antitrust law, while the Apple case centers on the European Union’s ability to intervene in areas of tax policy in one of its member nations.

Vestager cheered the court decisions at a news conference Tuesday in Brussels. She said she was so surprised by the Apple decision that she cried because the commission had lost the earlier appeal.