Cholesteatoma is a pathological tissue that may extend into all parts of temporal bone and rarely, as this study highlights, beyond its structures. Nevertheless, the spread outside the mastoid tip into the soft tissues of the neck or parotid space is very rare. The case of 23-year-old male with right parotid mass is presented. The patient had history (2006, 2009, and 2012) of three tympanoplastics for recurrent right ear cholesteatoma. The parotid tumor was revealed incidentally in magnetic resonance imaging in January 2016, but the imaging was inconclusive. After 6 months, the patient developed right-sided facial nerve palsy. The second look of the right ear was performed with simultaneous parotid surgery. The ear was healed and free of cholesteatoma, but the parotid mass resembled the cholesteatoma confirmed later on by histological examination. The tumor extended from stylomastoid foramen. This case was unusual as the disease had extended beyond the ear with the bony parts of the mastoid being preserved. To our knowledge, this is the first case report to describe a parotid gland cholesteatoma not being an extension of a cholesteatoma present in the tympanic cavity and entering the parotid gland via stylomastoid foramen.