Ex-rugby player Stuart Barnes has lost an IR35 battle against HMRC after the tax authority took the case to appeal.
Barnes lost this appeal in the Upper Tribunal, leaving him with a £700,000 tax bill.
Barnes came to be known as the "voice of rugby" after retiring from the sport in 1994, court documents set out.
Through his company S&L Barnes, he provided services to a range of media organisations between 2013 and 2019.
HMRC claimed two contracts with Sky fell within IR35 rules, meaning he should be taxed as an employee rather than a freelancer.
The outcome of the case on Wednesday (August 28) overturned a previous decision made by the First Tier Tribunal in January 2023.
The Upper Tribunal found an error of law in the initial decision, ruling Barnes' work with Sky was employment when it came to tax.
Dave Chaplin, CEO of IR35 Shield, watched the hearing at the Upper Tier Tribunal in central London.
He said the ruling means no cases involving people providing services to Sky TV have been successful in the tax tribunal.
Chaplin said: "The Stuart Barnes case was a close call that could have gone either way. It's crucial to note that HMRC's first ground of appeal failed, with the Upper Tribunal upholding the First Tier Tribunal's decision regarding the variation of terms related to Sky's 'right of first call'.
"However, HMRC's second ground of appeal, which was more controversial, did succeed. This ground focused on how the First Tier Tribunal approached the third stage of the Ready Mixed Concrete test and which factors it considered relevant to go into the mix for the full evaluation.
"The surprising element was that the UT chose to interfere with the evaluative nature of a multi-factorial decision by a First Tier tribunal.
"Both parties requested at the hearing that if an error of law was found, they preferred the Upper Tribunal to remake the decision rather than remit it back to the First Tier Tribunal. Had the case been remitted, it's possible that the First Tier Tribunal might have drawn a different conclusion – but it would have been a 50/50 chance."
He added it highlights the importance of freelancers and their clients ensuring contracts and working practices "accurately reflect the true nature of their relationship".
Seb Maley, CEO of IR35 compliance expert, Qdos, said the verdict shone the spotlight on the many nuances within the legislation.
He said: "Barnes won his First Tier Tribunal in 2023 because he was seen as being in business on his own account. But the Upper Tribunal turned the case on its head based on a different set of factors.
"He didn’t have the right to provide a substitute, Sky held the exclusive right to call on his services and he wasn’t seen to shoulder financial risk – hallmarks of an inside IR35 contract.
