Scottish First Division side Dundee have been deducted 25 points for going into administration.
Scottish Football League chief executive David Longmuir announced their punishment on Monday following a meeting of the organisation's board.
Dundee have also been hit with a player registration embargo and the SFL will reconsider their situation if they are not out of administration by March 31.
The SFL also plan an early-warning system with Her Majesty's Revenue and Customs (HMRC) to alert them to any more clubs facing financial difficulties.
Dundee went into administration on October 14 after being unable to pay a tax bill which stood at £420,000.
Longmuir said: "The SFL regrets the situation Dundee Football Club find themselves in for the second time in seven years.
"We are fully aware of the impact this situation has had on all concerned, especially players, staff and fans of the club.
"The SFL has a duty to protect the integrity and the ongoing smooth running of the league.
"Following a thorough process, as endorsed by the administrator, the board has decided that Dundee Football Club Limited is guilty of conduct contrary to the league rules, the interests of the league and its member clubs.
"The following sanctions will be imposed: Dundee Football Club will be deducted 25 league championship points with immediate effect, a player registration embargo be imposed until the club comes out of administration, and if the club is still in administration by March 31, the board will reconsider the matter and will deal with the club as it sees fit.
"It should be noted that Dundee Football Club has the right of appeal against these sanctions."
Dundee were fourth in the table on 14 points but now sit 20 points below Morton at the foot of the division.
In the previous two years both Gretna and Livingston were relegated from the First to the Third Division after breaking the league's insolvency rules.
However, the punishment is at the discretion of the SFL board and Dundee's situation is complicated by the fact that they went into administration mid-season, while the two most recent precedents were set in the summer.
Dundee administrator Bryan Jackson, who made nine players and management team Gordon Chisholm and Billy Dodds redundant, has hit out at the sanctions and announced his intention to appeal within an hour of the announcement.
In a statement, Jackson said: "I shall be appealing this decision by the SFL as I think that this is an outrageous punishment for the club.
"With almost guaranteed demotion from the First Division it will be much more difficult to attract investment or retain players.
"This could also ultimately affect the income of other First Division teams as we will be unable to attract a good away support if there is nothing to play for.
"Given that the club is fulfilling its fixtures with a credible team this seems a punitive and punishing blow which threatens the future existence of the club.
"Everyone involved at DFC is working hard to ensure that the club survives this administration but this penalty makes that situation much more difficult."
Jackson had been more positive about the club's survival chances in recent days, but he gave a stark warning about their prospects today.
The administrator had estimated the club's survival hopes at "50-50" when he first took over and warned there was only enough money to continue until Christmas.
He added: "Whilst I appreciate that the SFL had to be seen to act when the club fell into administration for the second time, it is questionable whether this punishment is not ultimately self-defeating by threatening the continued existence of the club.
"Given the support which the club has had from the team, from the supporters, and from the city of Dundee, the response of the SFL has effectively been dismissive of this support.
"We can go on in the short term but this action has made the future much less certain than it has been at any time since the administration began."