Objectives: Self-directed learning (SDL) is a process in which individuals take the initiative with or without the help of others in diagnosing their learning needs, formulating goals, identifying human as well as material resources for learning, implementing appropriate strategies and evaluating learning outcomes. In SDL, the onus of learning is on the learner and learning control is slowly transferred from facilitator to learner. Hence, this study helped to understand the SDL readiness in undergraduate medical students and figure out whether it differed between students of 2nd and 3rd professional years. Materials and Methods: The study was conducted on undergraduate medical students of 2nd and 3rd professional year of tertiary care medical college hospital in south India after receiving permission from the Institutional Ethics Committee. A total of 285 students were considered in this study from both years after informed consent. A pre-validated questionnaire of the self-rating scale for SDL (SRSSDL) tool was included, and it comprised five components, namely, awareness, learning strategy, learning activity, evaluation and interpersonal skills, with 12 questions in individual sections. Demographic data were expressed in percentages while the Chi-square test and independent sample Mann–Whitney U-test were applied to understand the differences between 2 professional years. Results: Out of 285 students, 56.8% had a moderate level of readiness, followed by a high level of readiness (42.9%). The majority of the students from both academic years had a moderate level of readiness toward SDL. Learning strategy had the highest mean response score of 3.7 ± 0.52, followed by awareness with 3.69 ± 0.49. This mean score reflects that the majority of participants’ responses recorded were either ‘sometimes’ or ‘often’ for various components of the SRSSDL tool. The distribution of awareness, learning strategy, learning activities, evaluation and interpersonal skills did not show any significant association across academic years and gender. Conclusion: The moderate level of readiness shows that areas of improvement must be identified and evaluated with teacher guidance when necessary. The SRSSDL tool can be used as a measure of evaluation, as it helps to classify student readiness toward SDL.