The accessory parotid gland (APG, Vth level) differs in histological structure from main parotid tissue. This gives rise to the hypothesis, mirrored in clinical observations, that the representation of tumours is different than in the rest of the gland. The aim of the study was to analyse the epidemiological and histological differences of parotid tumours located in regions I–V, with particular emphasis on the distinctiveness of region V. To define the epidemiological factors that will indicate the risk of histological malignancy from clinically benign appearance, multicentre prospective studies conducted between 2017–2021 by five Head and Neck Surgery University Departments, cooperating within the Polish Salivary Network Database 1929 patients (1048 women and 881 men), were included. The age, gender, patient occupation, place of inhabitation, tumour size, clinical features of malignancy, histology, and facial nerve (FN) paresis were analysed for superficial (I_II) and deep (III_IV) lobes and with special regard to the tumours affecting region V. Twenty eight tumours were located exclusively in region V (1.45% total) and seventy-two tumours were found in region V exhibiting extensions to neighbouring regions (3.7% total), characterised as significantly younger and less frequent in retirees. In I–IV regions, approximately 90% of tumours were benign, with pleomorphic adenoma (PA) and Whartin tumour (WT) predominance. In region V, PA exceeded 75% but WT were casuistic (2/28). Incidences of malignancies in region V was 40% but clinical signs of malignancy were evident only in tumours > 4 cm or in the presence of FN paresis. In 19% of patients with a benign appearance, imaging revealed malignancy; however, 38% of patients showed false negative results both in terms of clinical and radiological features of malignancy. Logistic regression models in 28 patients with tumours located exclusively in region V vs. 1901 other patients and in 100 patients with V extension vs. 1829 other patients showed no clinical symptoms of malignancy binding with final malignant tumour histology as a single variable or in combination with other variables. The logistic regression models obtained in this study show strong linkage between tumour location and predictors (age, male gender, and tumour diameter) and also aimed to function as a good classifier. Our conclusion is that, despite the very clear image of the mid-cheek tumour which is easily accessible in palpation and ultrasound examination, it is necessary to improve oncological vigilance and preoperative patient preparation.