Newcastle United have been hit with a demand for £3.2m from HM Revenue and Customs over a “deliberate” failure to pay tax, according to official disclosures that relate to a near decade-long investigation into player transfers under the club’s former owner, Mike Ashley.

The Tyneside club, which has been owned by Saudi Arabia’s sovereign wealth fund since 2021, owes HMRC £1.9m in tax and has also been hit with a penalty of £1.25m, the newly released documents show. The bill emerged as a result of the tax authority’s regular publication of a league table of “deliberate tax defaulters”, with Newcastle United featuring at the top of the most recent list, released on Thursday.

Both Newcastle and HMRC declined to comment on the reason that the club had been placed on the list. However the Guardian understands the fine is linked to a tax probe, known as Operation Loom, that saw officers from HMRC raid the club’s St James’ Park stadium in 2017.

HMRC said the default took place between April 2010 and April 2016, shortly before the raid, while the £1.2m sum in unpaid tax matches a figure published by the tax authority in 2017. Court papers at the time revealed that the raid related to allegations that the club “systemically abused” the tax system in the course of buying players. The investigation focused on an elaborate scheme designed to avoid paying income tax, VAT and national insurance relating to player payments and agents’ fees.

HMRC said Newcastle, owned at the time by Ashley, the Sports Direct tycoon, had used “sham” contracts that disguised the true recipients of cash. The alleged arrangements were in breach of FA agents’ regulations and happened in the “full knowledge” of Newcastle, according to HMRC officer Lee Griffiths at the time. HMRC dropped a criminal probe into Newcastle in 2021 but told the club that it would continue civil proceedings due to “tax non-compliance of a serious nature”, court papers show.

A spokesperson for St James Holdings Ltd, speaking on behalf of Ashley, said: “HMRC discontinued their criminal investigation prior to any charges being made. The new owners reached a civil settlement with HMRC. There was no finding of deliberate conduct by a Court or Tribunal and no admission of deliberate conduct was made to HMRC.”