Objectives. The aim of this cross-sectional study was to identify sleeping patterns among dental students and their association with self-reported bruxism in Riyadh Colleges of Dentistry and Pharmacy (RCsDP). Methods. A cross-sectional study was performed including 549 students (67 men and 482 women). A structured questionnaire was adopted from The PSQI (The Pittsburgh Sleep Questionnaire Index) used for data collection. It included questions which are categorized into sleeping habits, sleep-related symptoms, and additional questions concerning bruxism. This questionnaire was randomly distributed among all college preclinical and postclinical students. Sleep bruxism diagnosis was based on self-reported data. The data were analyzed using Chi-square tests through SPSS software for Windows. Results. Statistical analyses revealed significant correlations between self-reported bruxism and sleeping habits including sleep initiation (χ (2) = 22.6, p = 0.000), continuous sleep until morning (χ (2) = 19.2, p = 0.001), nighttime sleep duration (χ (2) = 20.2, p = 0.000), and length of daytime naps (χ (2) = 28.35, p = 0.000). There was an association between self-reported bruxism and sleeping-related symptoms including awakening early in the morning before the usual time without a cause (χ (2) = 16.52, p = 0.000) and increased nightmares (χ (2) = 13.7, p = 0.001). Conclusions. Poor sleeping pattern was an important factor among dental students, who reported sleep bruxism.