Trichoblastic Carcinoma (TBC) is an extremely rare adnexal malignancy arising from hair follicles with potential for local recurrence and metastasis. As of 2021, there were fewer than 100 case reports described in the literature. TBC has similarities with Basal Cell Carcinoma clinically and histologically which can lead to misdiagnosis. Mutations in the tumour suppressor gene CYLD on chromosome 16q12.1 has been identified in several cases, a gene implicated in Brooke Spiegler syndrome and Multiple Familial Trichoblastosis (MFT). We report the case of a 54-year-old male who presented with a long-standing lesion on his left leg, lateral and inferior to the knee. It had grown significantly and begun ulcerating over the 6 months prior to review. His medical history was significant for Acute Myeloid Leukaemia treated with bone marrow transplant in 2001, and a history of UV exposure though his occupation as a concreter. Histopathology from an excision biopsy specimen showed Trichoblastic Carcinoma with an involved deep margin. After discussion with the complex skin Multidisciplinary Team meeting, the patient proceeded to wide local excision (WLE) with 1cm surgical margins and reconstruction with split skin graft. The post-operative histopathology showed dermal scar and intra-epidermal carcinoma with no residual malignancy. Trichoblastic carcinoma is rare and formal management guidelines are lacking. WLE is recommended, but evidence for management is based on small case series and reports. This case highlights the utility of multidisciplinary team input and approaches to rare or complex cases and contributes to the limited body of literature on Trichoblastic Carcinoma.