Intracranial arachnoid cysts are benign fluid-filled sacs located between the brain and the arachnoid membrane. Their rupture is an uncommon event, often associated with trauma or an underlying pathology. Here, we present a case of a 61-year-old woman with a ruptured arachnoid cyst coinciding with a contralateral subdural hematoma. The patient manifested a persistent headache, balance disorders and right facial paresthesia. Brain CT study showed a right temporo-polar cyst (known to the patient) and a right parietal chronic Subdural Hematoma (cSDH). Although the kickback may contribute to bursting or weakening of cyst integrity, the CT-density pattern of the cSDH, according to Nomura classification is to be considered associated with increased fibrinolysis activity and potentially with parenchyma compression. This case highlights the importance of considering arachnoid cyst rupture as a potential indirect consequence of head trauma kickback, particularly in the presence of contralateral intracranial hemorrhage.