The large number of people with disabilities worldwide requires clinical training programs to prioritize removing accessibility barriers while being sensitive to cultural diversity and promoting equal opportunities. Evaluation is an essential tool to ensure program accountability while keeping them relevant to ongoing healthcare needs. Disability-focused training evaluation follows a step-by-step process, beginning with goal setting, followed by data gathering and analysis, and culminating in the use of outcomes. Kirkpatrick’s four-level model of evaluation is frequently applied to assess learner participation, knowledge acquisition, performance, and treatment outcomes. Evaluation tools include questionnaires, OSCEs, portfolios, and patient outcome measures tailored to different learning styles. Key evaluation indicators include cultural competence assessment and disability-specific outcomes, such as patient satisfaction and functional improvement, which help address gaps in healthcare service provision. Case-based solutions demonstrate how stakeholder feedback and cross-cutting evaluation methods enhance responsiveness. The integration of real-time analytics with multi-source assessments and evidence-based curriculum revisions guided by accessibility standards provides further solutions. Case studies on disabilities such as ADHD illustrate how new learning technologies generate positive effects and reduce knowledge deficits, though challenges remain regarding cost and readiness. Future medical education will increasingly adopt technology-enabled tools, including assistive technology, digital content, virtual environments, and AI-enabled personalized systems; however, these advances face resistance due to digital inequality and a lack of long-term impact studies. Bridging the gap between assessment and innovation enables educators and policymakers to design clinical education approaches that ensure equitable healthcare services for people with disabilities.