Mark Daly had been showing Sky Sports in The Old College Bar, in High Street, without the correct commercial viewing license.
But Sky TV bosses were awarded a court order at the Court of Session in Edinburgh to stop the pub manager's illegal screenings.
He will have to stump up £10,000 in damages, and pay Sky's legal costs, following the ruling.
Mr Daly also had to pay for a series of public notices - including one in The Evening Times - advertising the ruling.
The building which houses the bar was built in 1515, according a plaque above the door which reads: "Glasgow's oldest public house. Ancient staging post and hostelry."
It is thought to be the oldest bar in Glasgow and has been serving drink since 1812.
Sky Business provides commercial customers, including pubs, golf clubs, bookmakers, hotels, gyms, care homes, and oil rigs, with a variety of channels.
And bosses at the TV giant have vowed to continue their crackdown on pubs illegally screening sports matches
Alison Dolan, Deputy Managing Director at Sky Business, said: "This case demonstrates the seriousness of this issue through the large penalty applied.
"But also through the very first order to fund advertising, which we hope will help to warn pub landlords of the consequences of televising Sky's content illegally.
"We will not hesitate to take further legal action to help ensure that the thousands of law-abiding pubs and clubs who pay for commercial subscriptions are not short changed."
Sky's successful court order has led to the firm raising a number of actions to prevent other landlords from infringing their copyright.
Interim interdicts have been awarded against several licence holders who are now subject to legal action.
Colin Hulme is a partner of Scottish law firm Burness Paull team, who are acting for Sky in these cases.
He said: "This raft of cases demonstrates that Sky is working hard to protect their customers.
"I am confident that this result illustrates that those showing Sky programming without a licence will realise they are drinking in the last-chance saloon."
The Evening Times previously revealed a planning application has been made to demolish the Old College Bar in High Street and several nearby buildings.
No one from the College Bar was available for comment.