Cowan, a former tennis player best known for taking Pete Sampras to five sets at Wimbledon in 2001, appealed a previous decision by HMRC that he should be treated as an employee of Sky for tax purposes.

The case related to work carried out by Cowan between the 2014 and 2019 tax years.
 
The hearing was to consider Cowan’s application to appeal HMRC’s view that the freelance presenter worked in a manner akin to employment and therefore belonged inside IR35 for contracts held within that time.

However, Cowan’s representatives missed HMRC’s deadline to submit an application to appeal, with the court notes stating “serious and significant delay – no good reason”.

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Dave Chaplin, CEO and founder of IR35 Shield, a tax advisory firm which specialises in IR35 and Off-payroll matters said: “This is the second person to fall foul of the basics, and lose their IR35 case on a procedural point, following the same mistakes made in the case of Michael Lynagh.

Lynagh, a former professional rugby player, received an IR35 bill in the region of £230,000, after his appeal was rejected for a simliar reason.

 
“By not responding to the HMRC view of the matter letter and failing to appeal it within 30 days, this basic error has resulted in the case being lost, and the ability to appeal not permitted. Had it gone to tribunal, the outcome may have been different," said Chaplin.

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“This highlights the importance, particularly in IR35 cases, why taxpayers should engage with specialist advisors to defend them. Losing a fight on a procedural point, without even stepping into the ring will obviously be very disappointing for Mr Cowan.
 
“Reading the ruling, it appears an opinion was formed by HMRC, without the taxpayer having full access to the material upon which the opinion was made. That doesn’t chime with the concept of treating taxpayers fairly, and whilst HMRC has won a case, without a full hearing, the manner about which they have done so, raises concerns."

Qdos CEO, Seb Maley said: “You have to feel for Barry Cowan. Through no fault of his own, he won’t have the chance to appeal. If recent IR35 cases involving Sky Sports presenters are anything to go by, this huge error could have cost him a fortune. 

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“Filing an application to appeal is simple stuff – it should be bread and butter for Cowan’s representatives. What’s really worrying is that it’s not the first time we’ve seen this happen. Late last year it emerged that another Sky Sports presenter, Michael Lynagh, had his request to appeal denied because his accountant missed the deadline. 

“It goes without saying that in the event of an IR35 investigation, you need support you can count on. IR35 cases can carry millions in tax liability and HMRC is noticeably ramping up its compliance activity in this area.”

It comes after Gary Lineker won his £4.9m appeal against HMRC.

The sports presenter was pursued by HMRC over taxes on his income from the BBC and BT Sport. The tax authority said Lineker was an employee for both broadcasters, as part of the IR35 legislation, which was designed to prevent tax avoidance.

The same week, Eamonn Holmes lost his IR35 appeal against HMRC.