And today were in the high court over an unpaid £250,000 tax bill, with a very real threat of administration or liquidation.
Bosses at an events management firm said on Monday they were owed about £18,000 and wanted to launch a winding-up application.
At a winding-up hearing at the High Court, Orient owner Francesco Becchetti has been given until 12 June to pay off debts or sell the club.
In July 2014, lifelong fan and promoter Barry Hearn sold the club for £4m to Italian businessman Francesco Becchetti two months after they lost the League One play-off final to Rotherham United on penalties.
Outside court, fans said they would like to see Orient under new ownership.
Waltham Forest Council are owed £35,000, and there are other creditors too who must be paid who are entitled join the continued petition.
Orient also owe their club photographer £6,000.
Mr Registrar Briggs gave the club until June 12 to pay off sums of money to creditors - time being given as Becchetti's legal representative claimed he is to put a £1m cash injection into the club in the next eight to 10 weeks to cover all debts. A lawyer representing Orient said £1 million was due to be injected into the...
Adam Michaelson, legal adviser to the Leyton Orient Fans' Trust, told BBC Radio London: "It leaves the club in a state of significant uncertainty and frankly mortal danger".
Leyton Orient fans get behind their team during Saturday's match with Doncaster Rovers (pic: Simon O'Connor).