YouTube may have won long-form TV deals with the UK’s Channel 4 and Five, but it’s not going swimmingly everywhere in Europe. An Italian court has ordered it to remove all content by Italian broadcaster Mediaset, after a legal case going back more than a year.

The Silvio Berlusconi-owned network brought the case in July 2008, seeking a crazy €500 million in damages, as we reported at the time.

But such cases rarely end in payouts - instead, the court says YouTube should remove 4,643 clips and 325 hours of Mediaset content, C21 reports: “Mediaset had estimated it had lost 315,672 viewing days as a result of the uploads.”

Spain’s Telecinco had already got a similar order in 2008 and France’s TF1 also followed Viacom (NYSE: VIA) in bringing similar proceedings.

Italy has turned in to a bit of a niggle for Google (NSDQ: GOOG). In August, the Italian Competition Authority searched Google’s Milan offices during an investigation in to whether Google News uses newspapers’ content unfairly. The investigation was expanded in November.

But neither that nor the YouTube ruling are the most serious amongst a trio of Italian cases Google’s fighting. It’s currently laying out its defence against a defamation suit for having allowed a video of children bullying an autistic schoolboy in 2006…

Google argues that it removed the video upon receiving a complaint but that it’s not responsible for the content of Google Video. But the court has directly charged chief legal officer David Drummond, privacy chief Peter Fleischer (pictured), former CFO George Reyes (now retired) and senior product marketing manager Arvind Desikan.

NYT says the prosecution is seeking a one-year sentence for three of them, and a six-month sentence for the fourth, but that none would actually serve jail time “because sentences of less than three years are commuted in Italy for those without a criminal record”.

• Italy’s MediaSet Sues YouTube; Seeking At Least €500 Million Damages