Dermoid cysts are common periorbital lesions. They usually occur near the superolateral orbital rim, indenting but not extending within the bony outer table. We present an unusual case of a dumbbell-shaped dermoid cyst underlying the temporalis muscle with extension into the lateral wing of the greater sphenoid bone, approaching the optic canal. The cyst was successfully removed en bloc via a small skull base craniectomy without spillage of cyst contents. The patient recovered well without neurological or visual sequelae.