Plymouth Argyle have been deducted 10 points with immediate effect after they issued a notice of intention to appoint an administrator.
The notice is classed as an 'insolvency event' which breaks Football League sanctions and commands the automatic 10-point penalty.
The League One strugglers have been the subject of three winding-up petitions from HM Revenue & Customs this season.
It leaves Argyle bottom of League One, eight points from safety.
A statement on the club website said: "The directors of Plymouth Argyle Football Club have today issued a Notice of Intention to appoint Brendan Guilfoyle, Christopher White and John Russell of The P&A Partnership as administrators.
"This action gives the club protection from insolvency action from creditors.
"This does not mean that the club is in administration today nor does it assume that it will necessarily enter into administration at a future date."
Former Leeds chairman Peter Ridsdale, who has been advising Plymouth's board since December 2010, has previously told
the BBC that £2m is needed
to ensure the club survives until the end of the season.
With his side now facing an uphill battle against relegation, Argyle manager Peter Reid told BBC Spotlight: "From a football point of view it's a massive blow to the club.
"You've just got to get on with it. It's going to make it really difficult but we've just got try and start the fight back against Brighton.
"Hopefully the board of directors can sort out the financial problems and hopefully this is the lowest ebb and we can start rising from this situation."
Problems for Argyle first surfaced when they were placed under a transfer embargo by the Football League at the end of 2009 because of then-unpaid debts to HMRC.
Subsequent relegation from the Championship last season then cut Argyle's income by around £3m, and in November details
emerged of two winding-up petitions
from HMRC over further unpaid tax debts of £760,000.
Tax remains a major problem for the Devon club with their next bill, estimated at £300,000, due on Tuesday.
However, by issuing the 'notice of intention' the club is protected from its creditors, meaning that failure to pay HMRC by the deadline will not lead to the presentation of a compulsory winding-up petition.
This page is best viewed in an up-to-date web browser with style sheets (CSS) enabled. While you will be able to view the content of this page in your current browser, you will not be able to get the full visual experience. Please consider upgrading your browser software or enabling style sheets (CSS) if you are able to do so.