Primary calvarial boney tumors are generally rare in clinical practice. Multiple primary skull neoplasms are less frequent, typically associated with genetic disorders or familial syndromes. Sporadic cases of multiple skull tumors are exceptionally rare. We present a unique scenario of a 32-year-old female patient who had two right-sided skull vault lesions, one located over the right parietal area and the other in the right retro-auricular region. The lesions exhibited different behaviors over several years. The workup revealed that the two skull lesions were of two pathologies. The standard academic approach for clinical analysis attributes the symptoms often to one pathological process until proven otherwise. This case highlights the significance of expanding the differential diagnoses and incites clinicians to consider multiple pathologies in specific clinical settings.