Background: Sleep hygiene habits are essential to maintaining a healthy lifestyle. Sleep deprivation is a prevalent problem worldwide. Multiple studies have shown a high prevalence of sleep insufficiency among medical students due to high academic load, caffeine intake, and high-stress levels. Objectives: This study explores the relationship between sleep quality, academic performance, and psychological distress among medical students at Alfaisal University, Riyadh, Saudi Arabia. Methods: This cross-sectional study was conducted on medical students of all academic years at Alfaisal University, Riyadh. Two popular surveys – the Pittsburgh sleep quality index (PSQI) and K10 - were used to assess sleep quality and psychological distress, respectively. In addition, the survey contained questions on socio-demographics and academic performance. Sociodemographic characteristics were assessed across groups having poor and good sleep quality. In multivariate analysis, we employed conscious variable selection to develop models. All statistical tests were two-sided at P < 0.05 as statistically significant. Results: A total of 241 respondents participated in the study. Most respondents reported poor sleep quality (75.93%). The highest psychological distress was reported among respondents with poor sleep quality (48.63%). The relationship between Kessler's Psychological Distress score and sleep quality score was significantly positive and linear (P < 0.0001). The mean PSQI score was higher in students with lower GPAs (1.50 - 2.99) than in those with higher GPAs (3.00 - 4.00). This shows that those students who sleep well perform academically better. Conclusions: The quality of sleep among medical students is poor, which is associated with psychological distress and poor academic performance. It is highly suggested that the awareness of sleep hygiene with healthy sleep habits be campaigned among medical students. Also, academic mentors, program directors, and coordinators play a crucial role in ensuring that medical students are not academically overwhelmed.