RANGERS' dispute with Her Majesty's Revenue and Customs escalated yesterday after sheriff officers presented the club with a list of scenarios for recovery of debt if a repayment agreement is breached.

In a move leading tax experts describe as highly significant and a step away from a winding up order, two sheriff officers served papers on the club over an outstanding tax liability of £2.8 million, including details on potential recovery.

The Ibrox club has insisted the sheriff officers were not there to carry out an asset evaluation, which would list assets it could seize if the bill is not paid, and said it believed they had been instructed by HMRC for dramatic effect.

A Rangers spokesman said the club had held several meetings with HMRC representatives this week and that it had reached an outline agreement with the tax office on repayment.

Club sources, though, said they did “not recognise” the reported figure of £1.4m that the club would have to pay on top of the £2.8m as a penalty payment.

They also insisted the two officers were there as a formality, “delivering paperwork that must be put in place should negotiations prove to be unsuccessful” and that the visit lasted five minutes.

But a leading taxation expert, who asked not to be named, said: “This is quite a significant development and an extreme measure for HMRC to send sheriff officers. It’s always the stage before taking court proceedings and seeking a winding up order for outstanding debts.

“It’s not something that happens to HMRC clients every day to have sheriff officers at the door and is a clear indication of the seriousness with which HMRC is taking the matter.

“They are not there to negotiate. They arrive to tell you how monies will be collected and their use today suggests a breakdown in communication between the parties involved.”

Another expert said sheriff officers were used “to be a frightening thing as much as anything”, adding: “When a third party is dispatched it will always come with a warning of what follows if the debts are unpaid but there is still scope for a resolution.”

The £2.8m bill stems from liabilities run up on deals done during the high-spending reign of Dick Advocaat but was only identified in the later stages of the process which led to the takeover of Rangers by Craig Whyte in May.

HMRC also claim to be owed £24m in unpaid tax as a result of Rangers using employee remuneration trusts up to a decade ago, and interest and penalty charges could take the sum much higher if Rangers lose the case.

Last night, Rangers sources told The Herald there was no question of the agreement on the bill not being adhered to and there were continuing concerns of how the club’s dealings with HMRC were being made public.

A Rangers spokesman said: “RFC has been in detailed discussions with HMRC over a tax liability that was revealed during due diligence prior to the takeover of the club by a new majority shareholder earlier this year. Meetings have been held with representatives from HMRC this week and are ongoing and we have reached outline agreement with HMRC. Discussions today dealt with formalities.

“We are utterly dismayed that there are people who have been involved in this process who think it right to conduct normally confidential business discussions in public. They clearly would not do that with other businesses but think it all right with Rangers.”