Background: The landscape of otolaryngology training in Saudi Arabia is undergoing transformation due to the expansion of medical colleges and increased overseas medical scholarships. However, concerns persist regarding the satisfaction and adequacy of surgical education. This study aims to assess gaps in otolaryngology training through an in-depth needs assessment. Methods: A cross-sectional study was conducted among 85 otolaryngology–head and neck surgery residency graduates in Saudi Arabia between 2019 and 2021. Participants completed a validated questionnaire assessing deficiencies, importance, and competence in different subspecialty areas. Data were analyzed using descriptive statistics, median comparisons, and Kruskal–Wallis tests. Results: Participants identified deficiencies in training across domains, with significant variations in specific subspecialties among different regions. Dissatisfaction with clinical discussions, research training, access to simulation labs, and training in emerging subspecialties was evident. Conclusion: The study highlights challenges within otolaryngology training, emphasizing the need for continuous evaluation and adaptation to ensure high-quality and comprehensive training. Addressing these gaps is essential to produce well-rounded otolaryngologists capable of meeting the evolving demands of modern healthcare.