The Premier League said that five men were convicted of conspiracy to defraud, money laundering and contempt of court after generating the cash over five years.

Mark Gould, from London, is understood to have masterminded the operation and was sentenced to 11 years in prison at Chesterfield Crown Court on Tuesday.

The 36-year-old and co-defendants Steven Gordon, Peter Jolley, William Brown and Christopher Felvus also received prison terms.

A sixth gang member, Zak Smith, failed to appear at court for sentencing on Tuesday, with the Premier League saying that a warrant has been issued for his arrest.

The court heard how the group offered illegal access to matches from hundreds of channels around the world, as well as tens of thousands of on-demand films and TV shows.

The illegal streaming businesses employed 30 people, with one person going undercover at a specialist anti-piracy company, the league said.

Brown, from Stoke-on-Trent, denied conspiracy to defraud and claimed to have been acting as an undercover informant in the interests of law enforcement authorities and broadcasters.

But following a seven-week trial, the 33-year-old was unanimously convicted by a jury after 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, according to the league.

Jolley, 41, from Lancashire, was sentenced to 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.

Meanwhile, 46-year-old Gordon from Morecambe was jailed for five years and nine months for two counts of conspiracy to defraud.

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Felvus, 36, from Pontypool, pleaded guilty to two counts of conspiracy to defraud and was handed a prison sentence of three years and 11 months.

The prosecution was supported by Hammersmith & Fulham Council's trading standards team as well as the intellectual property protection organisation Fact.

Kevin Plumb, general counsel of the Premier League, described today's sentencing as the "result of a long and complex prosecution of a highly sophisticated operation".

He added: "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."

Mr Plumb said that fans who were customers of such illegal services are effectively supporting individuals in other "sinister and dangerous organised crime".

He added that the Premier League will "continue to protect our rights and our fans by investigating and prosecuting illegal operators at all levels".