Objective: Xanthogranulomatous prostatitis (XGP) is a rare entity that has different clinical presentations. This report of three cases illustrates the diversity of clinical features of XGP, together with a comprehensive literature review. Methods: Three elderly male Sri Lankan patients underwent transurethral resection of the prostate for severe lower urinary tract symptoms. Carcinoma of the prostate was suspected in two patients, and one of them had a very high prostate-specific antigen level (324 ng/mL), suggestive of metastatic prostate carcinoma. The third patient had a clinically benign prostate gland. The histology of all three resected prostate chippings revealed XGP. Results: This case series encompasses two cases of XGP that mimicked carcinoma of the prostate clinically and another case that had benign clinical features. Patients with XGP can have clinical, radiological and serological evidence of advanced prostate carcinoma. Other rare modes of presentation of XGP include prostate abscess and haematospermia. Many concerns of XGP such as aetiology, epidemiology, natural history, risk of malignant transformation and possible treatment options remain unclear due to the paucity of the literature. Conclusions: XGP presents with a variety of benign and malignant clinical features. The possibility of encountering XGP in patients with clinically malignant prostates should not be overlooked.