Alloplastic orbital implants are commonly used by surgeons in the repair of orbital wall defects. They are generally well tolerated, but they may cause late-onset complications. The authors present the case of a 65-year-old man with a history of left orbital floor fracture repair 25 years prior using a silicone orbital implant. He presented with a 1-year history of recurrent binocular vertical diplopia previously diagnosed as transient ischemic attacks. The patient subsequently presented with symptoms suggestive of orbital cellulitis, and after failure to respond to antibiotic therapy, he underwent surgical removal of the implant, revealing a large orbital hematoma. This case represents an unusual presentation of a known complication associated with orbital implant placement in a patient with previously diagnosed cerebrovascular disease as the cause of his neuroophthalmologic symptoms.