The two stars' entourages are claimed to have engaged in a fight at New York City's WiP venue in June, leaving several bystanders injured.
(Pictured above: Chris Brown shares image of his injured chin, the WiP nightclub in the wake of the brawl)
Owner's of WiP's sister club Greenhouse have since filed a $16 million (£10.2m) lawsuit claiming that Brown and Drake ruined the company's chances of securing a brand extension deal by allegedly instigating the altercation.
Model Romain Julien is also suing Drake and Brown after apparently suffering a severed tendon in his right hand in the scuffle. He also said he has suffered mental duress and cosmetic damage.
Julien has also named WiP in the suit, accusing club owners of not providing adequate security to break up the incident before patrons were hurt.
He is seeking actual and punitive damages to cover his medical issues, reports The AP.
A representative for WiP said the company will "respond appropriately" to the suit, while Drake and Brown declined to comment.
Julien's filing is just the latest legal wrangling in relation to the encounter, following a separate suit from injured bystanders Nadia Beddini and Lucy Pavlovsky against the owners of WiP.