Background: “Self-medication” is a frequent practice in which people take drugs without contacting a healthcare professional. It is common among medical students due to their understanding of pharmaceuticals & easy access to prescriptions. Therefore, the present study focuses on examining self-medication habits among first and third-year MBBS students in a tertiary care hospital in Assam, India. Methods: This prospective cross-sectional study involved medical students in two groups: 1st & 3rd year MBBS students. A pre-tested questionnaire was distributed to both groups using Google Forms, preceded by a pre-test conducted with 16 respondents. The data collection process involved 2 sections: Section A focused on demographic information, while Section B focused on self-medication-related inquiries using multiple-choice answers, open-ended questions & Likert scales. Results: The study found that two groups differ in drug information sources, with Group 2 relying more on classroom teaching (51.96%) & textbooks (53.92%), while Group 1 heavily relies on advertisements (38.04%), prescriptions (48.91%), & Google (41.30%). Group 2 had a higher percentage of reliance on different sources for drugs, suggesting social circles may influence their behavior. Both groups shared similar reasons for self-medication, but Group 2 had higher percentages for time-saving (66.67%), confidence in knowledge (58.82%), and ease & convenience (60.78%). Group 2 used a wider variety of drugs with significantly higher percentages for antispasmodics (31.37%), decongestants (77.45%), & lozenges (37.25%). Additionally, both groups had concerns about adverse effects, wrong drug use, misdiagnosis, and drug dependence. Furthermore, group 2 had a higher awareness of self-medication aspects, including dose, adverse drug reactions, precautions, and medication course completion, compared to Group 1. Conclusion: The present findings highlight the importance of understanding different information-seeking behaviors & motivations behind self-medication practices to tailor effective public health strategies.