Chondroblastoma of the temporal bone is a rare condition. Chondroblastomas account for less than 1% of primary bone tumors, and those involving the temporal bone represent a tiny fraction of these tumors with most arising from the knee, rib, and pelvis. We present a case series of two patients who presented with chondroblastomas of the temporal bone over a period of 8 years to the St. Vincent's Hospital in Melbourne, Victoria, Australia. In particular, we outline the presenting complaint, diagnostic imaging undertaken, and the importance of preoperative histopathology in coming to the diagnosis and subsequent resection undertaken. A review of the current literature is presented with a suggested management strategy for these tumors.