Former professional footballer and Sky Sports pundit Neil McCann lost his appeal at the Upper Tier Tribunal, leaving him with a tax bill in the region of £210,000.

McCann’s playing career saw him represent Dundee, Heart of Midlothian, Rangers, Southampton and Falkirk. He also played 26 times for Scotland and managed Dundee for a short period.

HMRC deemed that McCann, while working via his limited company, McCann Media, had been operating as a disguised employee while engaged by Sky Sports from 2013 to 2018.

McCann contested this at a First Tier Tribunal hearing, arguing that he provided services in a genuinely freelance capacity and therefore belonged outside the scope of the IR35 off-payroll working rules. However, this appeal was dismissed in 2022.

McCann escalated his appeal to the Upper Tier Tribunal, which was heard in October 2023. On 5 April 2024, this appeal was dismissed, on the grounds that he could not be considered in business on his own account.

On the ground of mutuality of obligation, the Upper Tribunal rejected McCann Media Limited’s (MML) arguments that McCann's ability to decline work and his engagement with Dundee FC negated mutuality.

The Upper Tribunal noted that there were factual findings of the First Tier Tribunal and clauses in the contracts that were inconsistent with the proposition that Sky was under no obligation to offer any work or McCann to perform any.

Seb Maley, CEO or IR35 specialist Qdos, said, “This is the latest in a long line of IR35 cases that highlight the devastating financial impact this legislation can have. Neil McCann won’t have set out to break the IR35 rules but has been saddled with a tax bill in the region of £210,000.”

Dave Chaplin, CEO of IR35 compliance firm IR35 Shield, noted that the Upper Tribunal's decision confirms the difficulty of overturning an IR35 ruling at the Upper Tribunal.