Olecranon stress fractures are a rare upper extremity fracture that primarily affects throwing athletes. The incidence of olecranon stress fractures are increasing owing to the number of patients playing and the volume of engagement in competitive sports, especially in the pediatric population. However, olecranon stress fractures can present a challenge from a management and a rehabilitation perspective owing to their vague presentation, thereby affecting how these patients are diagnosed and managed. Therefore, it is imperative to further evaluate the disease process, diagnosis, and treatment of this condition to best manage our patients.