Pilomatricomas are the second most common subcutaneous mass in the head and neck region of children, however less than 49% are correctly diagnosed prior to excision. These benign lesions which arise from hair follicle matrix cells are usually less than 3cm, and very rarely ‘giant’ (>5cm). Giant pilomatricomas have only been reported less than 40 times in the literature, and very rarely in children. We report a case of a 16 year old boy who presented with a rapidly growing infra-auricular mass post attempted incomplete excision 6 months prior. Initially painless and pink / blue , this mass became painful and dark red in the weeks prior to excision, eventually reaching approximately 6 x 9cm in size prior to excision. Due to it’s rapid progression and painful nature there was originally concerns of malignancy and the patient underwent MRI prior to resection. Complete surgical resection with free-flap reconstruction was curative. The timely diagnosis and correct management of rapidly enlarging head and neck masses in children is of great clinical importance. This case contributes to the very small pool of literature on giant pilomatricoma in children and is therefore of great interest to the scientific and healthcare community.