We describe the case of a 52-year-old man with a history of squamous cell carcinoma (SCC) of the tonsil who presented with right subacute otalgia and otorrhea. Dedicated computed tomography of the temporal bones showed opacification within the mastoid process with destruction of bony mastoid septations consistent with coalescent mastoiditis. Preoperative imaging showed no destruction or expansion of the bony eustachian tube that would indicate that a direct spread had occurred. An urgent cortical mastoidectomy was performed. Intraoperatively, a friable white mass surrounded with purulence and granulation tissue was biopsied and returned as SCC. The discrete metastasis was removed without complication. Postoperatively, the patient was prescribed palliative chemotherapy. This case shows that a metastatic SCC can be masked by an overlying mastoiditis, and thus it should be considered in the differential diagnosis of a patient with a history of oropharyngeal cancer.