Rooff was issued with a compulsory purchase order for land in Stratford, east London, in 2005 to make way for the Olympic Village.
But Rooff bosses believe they should have been given more compensation.
Their claim was turned down by government planners but Rooff has now started a new appeal in the High Court.
If Rooff wins its High Court battle many more appeals could follow.
The case hinges on the classification of the land itself.
London Development Agency (LDA) planners argued the land was only suitable for business development, which means it would be worth less money.
But Rooff claim the land was also suitable for residential use and says it should therefore receive extra compensation.
The BBC reported that John Hobson QC, appearing for Rooff, said: “It was a classic brownfield area that was awaiting beneficial regeneration and had been earmarked for that purpose.
“It was indeed shown that high quality, mixed-use development would have been the appropriate means of achieving that regeneration.”
Around 70 small businesses which were forced to sell land have now launched negotiations with the LDA over their compensation payments.
Rooff is hoping the High Court judge will allow the issue to be reconsidered.
Mr Justice Blake is being asked to quash the 2009 decision of then Communities Secretary John Denham.