(1) Background: Osteochondromas are the most common benign bone tumors, primarily found in long bones, while scapular osteochondromas are rare and account for less than 1% of all osteochondromas. (2) Methods: We present a case of a young female patient with a unique presentation of scapular osteochondroma. The patient exhibited superomedial scapula angle osteochondroma with winging, a rare manifestation of scapular osteochondroma. The patient had a slow-growing mass on the left scapula for several years. Physical examination revealed a visible deformity with significant winging of the scapula. Imaging studies demonstrated a large osteochondroma arising from the superomedial angle of the left scapula, with a bony stalk. (3) Results: Surgical excision was performed, and histopathological analysis confirmed the diagnosis of osteochondroma. Following the surgery, the patient experienced a significant improvement in scapular winging. A comprehensive literature review revealed only a limited number of reported cases of scapular osteochondroma with winging, underscoring the significance of this case report as a valuable addition to the existing literature. The diagnosis of scapular osteochondroma should be considered in the differential diagnosis of patients presenting with a scapular mass, particularly when associated with winging. Surgical excision is the recommended treatment, and complete excision is crucial to prevent recurrence. (4) Conclusions: This case report highlights a rare presentation of scapular osteochondroma with winging and emphasizes the importance of considering this diagnosis in patients with scapular masses accompanied by winging. The successful surgical intervention in our case resulted in significant improvement. Clinicians should be aware of this entity and consider prompt surgical intervention for complete excision, ensuring optimal patient outcomes and preventing recurrence. Further research and additional case reports are necessary to enhance our understanding of scapular osteochondroma and its varied clinical presentations. Furthermore, comprehensive studies involving larger patient cohorts are necessary to explore the full spectrum of clinical presentations of scapular osteochondromas. By documenting and analyzing a wider range of cases, including variations in tumor location, size, and associated symptoms, researchers can identify patterns and establish more accurate diagnostic criteria. This will facilitate early detection and appropriate management of scapular osteochondromas, ultimately improving patient outcomes.