A system for delivering a medical dressing onto an appendage, such as a finger or penis, of a patient includes a medical dressing defined by a flexible tubular sleeve that is configured to elastically expand radially, and a delivery device including a pair of pivotable spreader arms attached to a handle portion. The spreader arms of the delivery device are configured for insertion within the sleeve to enable radial expansion from a first diameter to a larger second diameter and positioning of the medical dressing onto the desired anatomical area.