Late enophthalmos is a well-known consequence of large orbital floor fractures. In rare cases, late enophthalmos can occur after direct trauma to the maxillary ostiomeatal complex and present as silent sinus syndrome (SSS). We report two cases of SSS manifesting as enophthalmos years after facial trauma. The first patient developed SSS 4 years after a minimally displaced orbital floor fracture. The second patient had progressive enophthalmos as a result of atelectasis of the maxillary sinus years after facial trauma and surgical repair of nasal fractures. There have been two prior reports of SSS presenting after orbital trauma. Our patients differ from these prior reports in that the enophthalmos was discovered years after the initial facial trauma. In the first patient, surgery addressing the blockage of the ostiomeatal complex arrested the enophthalmos; in the second patient, it reversed the enophthalmos.