Gradenigo's syndrome (GS) is a rare but life-threatening complication of acute otitis media (AOM). It is classically defined as a clinical triad of acute otitis media, ipsilateral sixth (abducens) nerve palsy, and pain in the distribution of the first and second branches of the trigeminal nerve. Another rare but serious complication of AOM is venous sinus thrombosis, which is often associated with GS. The diagnosis of these conditions requires clinical suspicion, sound interpretation of signs and symptoms, and the use of the correct imaging techniques.Here, we present the case of an 81-year-old man with a previous history of recurrent otitis media, who presented with GS and septic lateral sinus thrombosis. The clinical presentation, physiopathology, and management of these conditions are discussed.