When the Final Set Comes Down to a Deadline Gone? Barry Cowan’s IR35 Appeal Strikes Out
Barry Cowan, the tennis ace turned TV pundit, thought he had clinched a victory over a tax battle—only to find his latest IR35 appeal was tossed at the Upper‑Tier Tribunal. The setback followed an earlier missed deadline, turning a promising defense into a missed match.
How the “Match” Unfolded
Between the 2013/14 and 2018/19 tax years, HMRC alleged that Cowan operated like a full‑time employee while contracted with Sky. This led to a formal decision in December 2021.
- 30‑Day Window – Cowan had a month to appeal, but his legal representative missed it.
- Late Appeal – A second, belated appeal in April took him to the First‑Tier Tribunal, where the judge dismissed it, citing “no good reason” for the “serious and significant delay.”
- Upper‑Tier Tribunal – The latest attempt, heard in June, ended in the same fashion—another loss.
As the verdict stands, Cowan faces unpaid income tax and National Insurance on the disputed engagements—regardless of whether his self‑employment was actually compliant.
Insights From Legal Street‑Cred
Qdos, the IR35 compliance firm headed by Seb Maley, summed it up: “Two failed appeals are the result of a broken pace brought by Cowan’s representative. They were too busy mumbling over technicalities while the clocks were ticking.”
Key take‑aways for anyone navigating the IR35 maze:
- Deadlines Matter – HMRC, and the tribunals, are relentless. Missing a statutory window can seal a case before you even get to your point.
- Accountable Representation – When it’s a matter of hundreds of thousands of pounds, you need a reliable team that gets the details right.
- No Second Chances – A single missed deadline may result in losing the chance to present your case, and you’ll be liable for the tax that follows.
“Through no fault of his own, Cowan had no real chance to prove his side. He’s now paying the price for his counsel’s misstep,” criticises Maley.
Bottom Line
Think of IR35 compliance like a tennis match: every point counts, but the real penalty is when you miss the clock. Get your paperwork right, keep your deadlines in check, and choose a legal team that plays the ball—so you can win, not just serve.
