Dissecting cellulitis is an inflammatory disease of the skin. We report a case of recurrent dissecting cellulitis in a patient with Crohn's disease. A 31-year-old man with a history of purulent scalp lesions presented with night sweats, weight loss, abdominal pain, and hematochezia. Colonoscopy revealed a diffuse friable mucosa with extensive pseudopolyps. Scalp biopsy demonstrated epidermoid inclusion cysts with granulation tissue and chronic inflammatory cell infiltration, indicative of dissecting cellulitis. The incidence of dissecting cellulitis with Crohn's disease is underreported. This dermatologic condition has a tendency to recur, and considering an underlying disease is key for its appropriate treatment.