Objective: This study investigated whether preclinical year insomnia predicted post-clerkship anxiety and whether preclinical year depression predicted post-clerkship insomnia among Korean medical students. Methods: A total of 57 students (38 males and 19 females) aged 23-34 years (27.40±2.76 years) completed questionnaires that included the hospital anxiety and depression scale, insomnia severity index, and morningness-eveningness assessment at the beginning and end of the clerkship. Results: A multiple linear regression analysis revealed that preclinical year sleep quality (β=0.291, p=0.032) was a statistically significant predictor of post-clerkship anxiety after controlling for preclerkship age, sex, and chronotype. Another multiple linear regression analysis revealed that preclinical year depression (β=0.541, p<0.001) was a statistically significant predictor of poor post-clerkship sleep quality, after controlling for age, sex, post-clerkship year anxiety, and chronotype. Conclusion: This study found that preclinical year insomnia may be related to post-clerkship anxiety. Post-clerkship insomnia was related to preclinical year depression. These findings may help medical school administrators reduce their students' anxiety and poor sleep through a cognitive behavioral approach and with psychological education.