The aim of this study was to display the cancer-specific and overall survival of patients with primary and metastatic malignancies of the parotid gland. In this retrospective study all patients with primary parotid malignancy and metastatic cutaneous squamous cell carcinoma (cSCC) of the parotid gland treated surgically with curative intent at a tertiary care institution were included. Patients were followed with regards to their oncologic outcome for a minimum of two years. Management approaches, overall, and cancer-specific survival were compared between patients with primary and secondary parotid gland carcinomas. Ninety-four patients (43 patients with primary parotid malignancy; 51 patients with metastatic cSCC of the parotid gland) were included. Patients with metastatic cSCC were older (p = 0.001) and more frequently male (p = 0.002). Adjuvant therapy (p = 0.001) and neck dissection (p = 0.009) were more frequently performed among patients with metastatic cSCC of the parotid gland than among those with primary parotid malignancy. Mean follow-up was 50 (95% CI: 40-65) months. Five-year cancer-specific survival was 87.3% among patients with primary parotid malignancies and 54.5% among patients with metastatic cSCC (p = 0.006). Cancer-specific survival of patients with metastatic cSCC of the parotid gland is still low. An earlier diagnosis of parotid metastases of cSCC may potentially lead to a better prognosis.