<i>Background and Objectives</i>: Monteggia fracture-dislocations are rare but critical injuries in children. Accurate early diagnosis is essential to avoid long-term complications; however, such injuries are frequently missed. Therefore, this study aimed to assess the diagnostic accuracy of Monteggia fractures among physicians of varying specialties and experience levels and to identify factors influencing diagnostic performance. <i>Materials and Methods</i>: This retrospective study analyzed the radiographic interpretations of pediatric elbow and forearm injuries by six physician groups: orthopedic residents, general orthopedic surgeons, pediatric orthopedic surgeons, general radiologists, and subspecialized musculoskeletal radiologists. The final diagnosis established by pediatric radiology experts served as the reference standard. Influential variables, such as image quality, splint application, and age-related ossification, were evaluated. <i>Results</i>: In total, 120 patients were included, 40 (33.3%) of whom were diagnosed with Monteggia fractures and 80 (66.7%) with other fracture types. The diagnostic accuracy of Monteggia fractures varied significantly according to the physician's experience. First-year residents and non-subspecialty radiologists had the highest rate of missed diagnoses. While other fracture types were occasionally influenced by technical factors, most missed Monteggia fracture cases stemmed from recognition failure. Subtle imaging features, plastic deformation of the ulna, and the omission of dedicated elbow views contributed to the misdiagnosis. Awareness and training improved performance, and a high index of suspicion was identified as crucial. Early follow-ups and standardized imaging protocols were identified as effective safeguards. <i>Conclusions</i>: Experience level, awareness, and imaging protocol quality were identified as being central to the accurate diagnosis of pediatric Monteggia fractures. Implementing educational strategies, promoting systematic imaging reviews, and reinforcing team-based approaches may reduce the rate of missed diagnoses.