Background: Lipoblastoma is a rare benign tumor that typically occurs in the extremities but can also be located in the head and neck region. Patients typically present with a painless enlarging mass unless the mass causes obstruction of adjacent functional organs. We review two cases of head and neck lipoblastomas presenting in the pediatric age group. Additionally, we review the literature on the presentation and management options associated with this tumor. Methods: Retrospective case review. Case series: A 6-month-old male presented with an enlarging left preauricular mass of 2–3 months duration. There was no overlying skin changes or associated lymphadenopathy. Cranial nerve function and ear examination were all within normal limits. A previous trial of antibiotics was unsuccessful. Magnetic resonance imaging revealed a sizeable lesion with invagination of tumor into the superficial parotid gland and temporalis muscle. A complete excision was performed after persistent enlargement and growing disfugurement. The diagnosis of lipoblastoma was made. A 15-month old male presented with a slowly progressively growing lateral neck mass without any other symptoms. Computerized tomography imaging revealed concern for a second branchial cleft cyst. Complete surgical excision was therefore recommended. An encapusulated fatty tumor was found intraoperatively and a lipoblastoma was eventually diagnosed. Results: Lipoblastoma of the head and neck region can present as a perplexing and rapidly enlarging head and neck mass in the pediatric population. The Otolaryngologist should be aware of this entity and work up when attempting to rule out either a malignant or infectious process that can occur with rapidly enlarging masses in the pediatric subgroup. We present a case series of two patients who presented diagnostic dilemmas to the treating surgeons. Sparing surgical extirpation is recommended with long-term follow up as the treatment of choice. Encapsulated removal of the mass can lead to a recurrence free outcome.