Subconjunctival hemorrhages are common in trauma and with increased intra-abdominal pressure. Despite the sustained pressure endured while pushing, they are rarely observed postpartum and can be an indicator of underlying ophthalmic disease. We present a case of a postpartum patient who developed bilateral subconjunctival hemorrhages with a retro-orbital hematoma. The patient is a 29-year-old gravida-1-para-0 at 41 weeks gestation who underwent an uncomplicated induction and delivery. She developed diplopia and orbital pain postpartum. Imaging revealed an orbital hematoma with an ophthalmologic workup revealing suspected glaucoma. She was followed outpatient with symptomatic treatment and had resolution of symptoms after 4 weeks. This case demonstrates a rare postpartum scenario and the subsequent workup. Subconjunctival hemorrhages are rare in the postpartum period despite prolonged pushing efforts. Incorporating a multidisciplinary approach for diagnosis of a pregnant patient with ophthalmologic disease is required to optimize management in the antepartum, intrapartum, and postpartum periods.