Assessing all domains of learning remains a challenge, particularly in dental education, where the psychomotor domain of Bloom’s Taxonomy holds significant importance. Dentistry, as a surgical specialty, encompasses a wide range of procedures—from simple to highly complex—that form the foundation of effective therapy. To introduce standardisation and minimise variables affecting performance assessment, Objective Structured Clinical Examinations (OSCEs) were developed. Compared to traditional long case examinations, OSCEs offer a more structured and objective approach to evaluating clinical competencies. Primarily, OSCEs serve as a tool for assessing clinical skills in simulated settings, ensuring consistency in evaluation. This narrative review provides a concise yet insightful account of the historical evolution of OSCEs, their underlying principles, practical considerations for implementation, and a critical analysis of their effectiveness in dental education.