A UK judge has ordered Google to remove old articles about a businessman's past crime from its search results, dealing a blow to the tech company in its legal battle over Europe's "right to be forgotten" law.

Two businessmen, both unnamed in the case, went to court to force Google (GOOGL) to de-list several articles about years-old crimes, arguing in part that the stories were out of date, of no public interest and infringe on their privacy rights.

Google had previously declined their requests to delete the stories, in one case citing the "substantial public interest" of providing information about the individual's "professional life."

On Friday, Justice Mark Warby ruled in favor of one of the businessmen, determining that the information about the crime and punishment had become outdated and "irrelevant."

As a result, the stories were "of no sufficient legitimate interest to users of Google Search to justify its continued availability" and should be removed, according to the judge.

However, the judge declined to award damages to the businessman.

In a statement, Google said it "will respect the judgments they have made in this case."

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"We work hard to comply with the Right to be Forgotten, but we take great care not to remove search results that are in the public interest and will defend the public's right to access lawful information," Google said in the statement provided to CNN.

The European Court of Justice issued a landmark ruling in 2014 that search engines like Google must remove certain unwanted links upon request, establishing a legal precedent across the European Union. The decision stemmed from a Spanish man's attempts to remove old links to his debt problems.

Since then, Google has received requests to remove more than two million URLs from Europeans, according to a transparency report published in February. Of those requests, 8% were related to "crime" and 7% were related to "professional wrongdoing."

Meg Jones, an assistant professor at Georgetown who researches data protection and privacy, said the court's ruling "sets something of a precedent."

"Google has been making determinations about whether to remove criminal information, and this time they got it wrong," she said.

While both businessman in the latest court case had been convicted of crimes, the winning businessman had "expressed genuine remorse" and no longer works in the same field as he did when the crime was committed.

"His past offending is of little if any relevance to anybody's assessment of his suitability to engage in relevant business activity now, or in the future," the judge wrote. "There is no real need for anybody to be warned about that activity."

-- CNN's Ivana Kottasova contributed to this report.