Stress fractures of the proximal phalanx of the great toe are primarily attributed to repetitive shear forces, with the vertical ground reaction forces exerting several times the body weight. In the initial stages of injury, conservative management anticipates bone healing within approximately five weeks, followed by a gradual return to sports activities over an additional five weeks. Athletes presenting with pain in this region warrant a thorough evaluation for stress fractures to initiate timely conservative care. In instances of delayed healing or non-union, surgical intervention is indicated. However, literature on the management and optimal timing of surgery, particularly in adolescent athletes, remains sparse. This case report, complemented by a literature review, offers insights into management based on the patient's clinical course.