Squamous cell carcinoma is the most common malignancy of the head and neck. Pseudovascular squamous cell carcinoma (PSCC) is a rare variant that occurs commonly in the skin of the head and neck. However, oral cavity involvement is extremely rare, with only a few cases reported to date. This variant is associated with an adverse prognosis. Morphologically, the tumour shows marked acantholysis and anastomosing channels mimicking vascular neoplasms. This rare variant poses a diagnostic challenge for pathologists and the accurate diagnosis can be made with the help of immunohistochemical (IHC) studies. A 72-year-old male patient was referred to our hospital with a fast-growing left-sided oral ulcer for more than 1 month. Wide local excision with segmental mandibulectomy was performed and the specimen was sent to our department. On gross examination, a large, soft, lobulated mass was identified in the lower alveolus and the buccal mucosa. On microscopic examination, the tumour was composed of malignant epithelial cells arranged in nests, trabeculae and irregular anastomosing channels. Marked acantholysis and pseudo vascular spaces lined by atypical cells were seen. IHC examination revealed tumour cells positive for CK, P40, P63 and Vimentin and negative for CD31, CD34, S100 and HMB45. The pathological diagnosis was confirmed as PSCC. A short history of the case and a review of literature is discussed here.