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Abstract Purpose The aim of this study is to investigate and highlight the most important factors influencing the candidate’s selection for residency matching by program directors of surgical and non-surgical specialties in Saudi Arabia. Method This cross-sectional study was conducted in the Central, Eastern, Western, Northern, and Southern regions of Saudi Arabia from February 1, 2023, to August 31, 2023. A total of sixty-one program directors completed a questionnaire, which was adapted and validated from a previous study with permission and tailored to meet the objectives of this research. Results The mean age of the study population was 40.2 years, with surgical specialty program directors being older at 41.7 years and nonsurgical specialty program directors being younger at 39.6 years. In both cases, the highest importance was given to ‘Applicant’s attitude and professionalism’, followed in surgical specialties by ‘Doing clinical rotations in the PD institution’ and ‘Performance in clinical rotation during internship’ in non-surgical specialties. with a mean score of 4.13 and 4.95, respectively. The importance of ‘The impression/opinion of current residents’ has had a certain importance in both specialties. While the number of research projects was prioritized more by surgical PDs (38.6%) compared to non-surgical PDs (29.4%). Conclusion This study highlights the critical role of professionalism and a positive attitude in clinical rotations and interviews for program acceptance in Saudi Arabia. The significance of letters of recommendation and research focus varies between surgical and non-surgical program directors. Program directors should adopt effective recruitment strategies that incorporate practical implications during internships.