Drug Reaction with Eosinophilia and Systemic Symptoms (DRESS) syndrome is a drug hypersensitivity reaction characterized by rash, multiple systemic symptoms, and eosinophilia. DRESS syndrome develops following exposure to inciting medications, typically antibiotics and antiepileptics. Anticoagulants are not classically associated with this syndrome, though cases exist in association with vitamin K antagonists and oral anticoagulants. There are two known cases of enoxaparin-induced DRESS syndrome in adults, but no reports in the literature in the pediatric setting. In this report, we present the case of a pediatric patient who developed classic symptoms and lab findings of DRESS syndrome secondary to enoxaparin therapy.