Background: Medical students are likely to have sleep problems, which can influence their academic performance. The purpose of the study was to investigate the connection between the quality of sleep, sleepiness during the day, mental health, and the academic performance of Iraqi medical students. Materials & Methods: The study involved 102 undergraduate medical students in Iraq in a cross-sectional study. An online self-administered questionnaire was used to gather data. The quality of sleep was measured with the help of the Pittsburgh Sleep Quality Index (PSQI), whereas the daytime sleepiness was estimated with the help of Epworth Sleepiness Scale (ESS). PHQ-2 and GAD-2 were used to screen depression and anxiety. Descriptive statistics, correlation tests and regression analysis were done using statistical analysis. Results: A low quality of sleep was observed in 69.6 percent of the students and 33.3 percent of them were overly sleepy. The correlation between both PSQI and ESS scores with GPA were negative. Students who slept well and were not sleepy during the day performed much better in terms of GPA. Poor sleep was highly correlated with depression and anxiety and depression was a predictor of poor sleep quality on its own. Conclusion: Iraqi medical students experience sleep disturbance which is associated with poor academic performance. Sleep and mental health screening and improvement can be used to improve the academic performance of students.