Objectives: Becoming an Orthopaedic Surgeon is a challenge worldwide. This study attempted to determine the level of training at which orthopaedic surgery is chosen as a career by residents and graduates of Gulf Cooperation Council (GCC) countries. The reasons for choosing this surgical speciality and barriers faced by residents were also explored. Methods: In this cross-sectional study, a questionnaire was electronically distributed to all GCC orthopaedic surgery residents. All currently enrolled residents and fellows in orthopaedic surgery programmes in KSA, Oman, Kuwait, and Bahrain were invited. Exclusion criteria included first-year residents and those who had completed their residencies before 2013. Results: A total of 275 out of 569 residents responded, a response rate of 48.33%. More than half of the participants (54.5%) chose orthopaedic surgery during their undergraduate studies. Personal interest ranked number one at 61.09%, while parental pressure was found to be the least important reason (0.36%). The majority (88.0%) agreed that orthopaedic surgery was physically demanding, whereas 33.1% wanted to quit orthopaedic surgery. The interest of residents for future subspecialities was mostly in paediatric orthopaedics and sports medicine, as suggested by 16.4% and 16.0%, respectively. Conclusion: This study showed an alarming number of residents who wanted to quit orthopaedic surgery. The challenges residents faced were burnout, lack of time, limited exposure to teaching hospitals, and limited seats for subspeciality training. We recommend increasing the number of orthopaedic surgery subspeciality fellowships, as well as the number of fellowship seats in training programmes. The well-being of orthopaedic surgery residents should also be given consideration.