Members of the streaming gang received prison terms ranging from three to 11 years each after the Premier League brought what it said was "the world's largest-ever prosecution of an illegal streaming network."
The gang's "mastermind", Mark Gould, 36, was sentenced to 11 years in jail at Chesterfield Justice Center, in central England.
The remaining four received sentences ranging from three to more than five years.
Premier League general counsel Kevin Plumb said "The sentences handed down, which are the longest sentences ever issued for piracy-related crimes, vindicate the efforts made to bring these individuals to justice and reflect the severity and extent of the crimes."
The defendants, aged between 30 and 46, raked in more than £7 million ($8.7 million) selling subscriptions to three illegal platforms streaming to over 50,000 customers and resellers.
"The organizations offered illegal access to watch Premier League matches, hundreds of channels from around the world and tens of thousands of on-demand films and TV shows," the Premier League said in a statement.
The gang, which relied on dozens of employees, profited by offering live access to Premier League games otherwise unavailable in the U.K. due to so-called "blackout" broadcasting rules.
It accessed feeds from broadcasters in the U.K., Qatar, the United States, Australia and Canada and streamed them a few seconds later.
The operation developed mobile phone and online apps screening Premier League matches and other content.
England's Premier League is the most lucrative football league in the world, with the U.K. broadcast rights alone worth about £5 billion for the 2022 to 2025 seasons.