The rapper is said to have pulled out of a Canadian tour organised by Spin Artist Agency just one day before it was due to begin last year.
The firm has now filed a federal lawsuit against the 'Wild Ones' star for cancelling the ten-date tour, which had been scheduled to take place from July 3 to July 12, 2011.
The papers were filed in Florida earlier this week, according to TMZ.
Spin Artist Agency claims to have a signed contract from Flo Rida and believes his representatives "wrongfully cancelled the tour" due to the short notice.
The company is seeking damages for breach of contract and are claiming losses in ticket, food and alcohol sales.
Earlier this year, Flo Rida was sued by an Australian festival promoter for AU$55,000 (£36,500/$57,000) after he cancelled an appearance at the Fat As Butter event.