Christopher Clachar was caught showing matches in his Clachan Bar in Whitburn, West Lothian, by undercover investigators and taken to court.
He was slapped with an order banning him from showing any other games without a proper agreement with Sky in August 2016. He breached that and was hit with a fine which went unpaid.
But despite this, Clachar continued to show football to customers in the bar but was caught twice.
Another team of undercover investigators watched as punters enjoyed watching a match in February 2017 and April 2017 unaware Clachar did not have a licence to show them.
He then failed to appear at a hearing last month leading to further contempt of court proceedings being brought against him.
Judge Lord Ericht at the Court of Session has now jailed Clachar for 14 days for contempt, the first time someone has been jailed for breaching a court order and contempt in a case stemming from the unlawful screening of Sky football games.
The court heard Clachar no longer manages the pub, is unemployed and has run up debt.
Sky are also considering whether to launch bankruptcy proceedings against him.
Lord Ericht told Clachar: “This case was brought against you by Sky in order to protect their intellectual property rights in televised football matches.
“You are no longer a danger to their intellectual property rights. You are no longer involved in the pub industry.
He added: “Sky complained that they were being penalised because of the expense which they have incurred in this case.
“However, they have brought this on themselves by choosing for their own commercial reasons to continue to proceed against a person who is no longer a danger to their intellectual property rights and who is unlikely to have the means to pay any award of expenses.
“Sky has strongly urged me to send you to prison.
“I wish to make absolutely clear that the penalty to be imposed on you is a matter for me and not for Sky. You are not being punished for the showing of Sky football matches in a pub. You are being punished for breach of a court order.
“This is the second occasion when you have appeared before this court for breach of interdict. On the first occasion you were fined. You failed to pay the fine when it was due and even now have not paid it off in full.
“In all the circumstances, there is no alternative to imprisonment.”
Sky Sports is only available to licensed premises who have entered into a commercial agreement with the broadcaster which differs from the usual customer charges.
George Lawson, head of commercial piracy at Sky, added: “This is the first instance in which a breach of interdict and associated contempt of court emanating from the unlawful showing of Sky broadcasts have resulted in a custodial sentence being issued.
“Mr Clachar was previously found in contempt of court for a previous breach of interdict in August 2016.
“On that instance he was issued with a court fine which was not paid in full.
“As a result, the court considered the only suitable punishment for this contempt, was a custodial sentence.
“This ruling demonstrates the seriousness of this issue.
“We are committed to visiting thousands of pubs every season to monitor the games they are showing, as well as investigating suppliers to protect Sky customers who are unfairly losing business due to this illegal activity.”
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