Five men illegally streamed Premier League football matches to tens of thousands of people in a scam believed to have been the biggest of its kind.
Mark Gould, 36, masterminded the operation from his plush riverside flat in Greenwich, southeast London.
He and his associates sold cut-price £10-a-month subscriptions, receiving more than £7million from 50,000 subscribers.
The men bragged they made money showing Premier League games not otherwise available to watch live in the UK because of "blackout" broadcasting rules.
But the Premier League itself prosecuted Gould and his accomplices, in a rare move by the league.
The fraud prosecution was brought to protect "some of the world's most valuable content", the league's lawyers said.
And Gould was today jailed for 11 years for his role in the racket. Four other members were sentenced to between three and more than five years.
Gould, co-defendants Steven Gordon, Peter Jolley, William Brown and Christopher Felvus were all convicted of conspiracy to defraud, money laundering and contempt of court.
Felvus, 36, was also found guilty of voyeurism and possessing indecent images of children, discovered on his computer.
A sixth gang member, Zak Smith, failed to appear at court for sentencing and a warrant has been issued for his arrest, the Premier League said.
The personal details of many of those who paid for Flawless TV are now in the hands of investigators, raising the question of what action might be taken against them.
Chesterfield Crown Court heard the gang took feeds from broadcasters in the UK, Qatar, the US, Australia and Canada and streamed them a few seconds later via the Flawless service.
Brown, from Stoke-on-Trent, Staffordshire, denied conspiracy to defraud, claiming to have been an undercover informant acting in the interests of law enforcement authorities and broadcasters.
But the 33-year-old was unanimously convicted by a jury after a seven-week trial as the Premier League said he used his technical skills to hack legitimate customers' accounts to access and copy streams - intending for them to take the blame if identified by authorities.
He was jailed for four years and nine months, the Premier League said.
Jolley, 41, from Skelmersdale, Lancashire, was handed a prison sentence of five years and two months for two counts of conspiracy to defraud and one count of money laundering after concealing £500,000 in his parents' bank accounts.
Gordon, 46, from Morecambe, Lancashire, was jailed for five years and nine months for two counts of conspiracy to defraud.
The Premier League said Felvus, from Pontypool, Monmouthshire, pleaded guilty to two counts of conspiracy to defraud and was jailed for three years and 11 months.
Premier League general counsel Kevin Plumb said: "Today's sentencing is the result of a long and complex prosecution of a highly sophisticated operation.
"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.
"This prosecution is another concrete example of the clear links between piracy and wider criminality, a warning we repeatedly make.
"While most Premier League fans enjoy watching our games in a safe way, those who were customers of these services were effectively supporting individuals involved in other sinister and dangerous organised crime.
"The Premier League's substantial financial contribution to the entire football pyramid is made possible through the ability to sell our broadcast rights.
"We are pleased that through rulings such as this, the courts continue to show that they recognise the importance of safeguarding the Premier League's rights.
"We will continue to protect our rights and our fans by investigating and prosecuting illegal operators at all levels."
