A 13-year-old male presented with headache, decreased vision, and left eye pain following a hair pulling incident at school 5 days prior. CT scans showed progression of a subgaleal hematoma that extended into the left orbit, causing complete ophthalmoplegia and orbital compartment syndrome. The patient underwent emergent canthotomy/cantholysis and anterior orbitotomy with hematoma evacuation. Subgaleal hematomas can extend into the orbit in children due to loosely attached tissues, causing vision loss if not treated urgently.