<p>The consumption of dietary supplements has increased substantially in recent years, accompanied by growing concerns regarding potential interactions with medications. Despite their clinical importance, drug–food (DF) and drug–dietary supplement (DDS) interactions are often insufficiently emphasized during medical education. Certain foods and supplements may alter drug pharmacokinetics, increasing drug concentrations in biological fluids and potentially leading to toxicity or adverse effects. Previous studies suggest that medical students’ knowledge of DDS and DF interactions is limited. However, little is known about how this knowledge evolves throughout the entire course of medical education. This study aimed to compare the knowledge, awareness, and behaviors related to DDS and DF interactions among medical students across different academic years, with particular emphasis on the period following pharmacology training in the third year. This study employed a web-based, cross-sectional survey conducted among medical students. The questionnaire, distributed via WhatsApp^®, was administered using Google Forms. Of the 584 enrolled students, 302 participated. The survey consisted of 53 items across three sections assessing demographic characteristics, medication-use habits, and perceptions, with responses measured using a five-point Likert scale. The results indicated that the levels of knowledge and awareness of DDS and DF interactions were lower among fifth- and sixth-year students compared with students in earlier academic years. In contrast, knowledge regarding appropriate medication-use behavior was relatively high before the third year. Additionally, students’ practices related to medications, food, and dietary supplements varied across academic years. These findings highlight the need for educational strategies to improve the long-term retention of knowledge regarding DDS and DF interactions during medical training.</p>