Objectives: To assess the prevalence of bruxism and occupational stress among Saudi Arabian fighter pilots. Methods: This was an observational, cross-sectional study where 110 fighter pilots were compared with 110 control non-pilots. The data collection was carried out by two dentists between February 2018 and May 2019. The subjects who consented to the study completed the Karasek’s Demand-Control questionnaire (short version) comprising 11 questions (5 for demand and 6 for control) designed to measure occupational stress. The assessment of bruxism was made using the non-instrumental approach of the International Consensus on the Assessment of Bruxism which includes both clinical examination and self-report of diurnal and nocturnal bruxism. A logistic regression test was performed with bruxism as the dependent variable controlling for occupational stress, type of occupation, and smoking status. Results: The total sample comprising pilots and non-pilots had an overall bruxism prevalence of 41.8%, with more pilots (52.7%) than non-pilots (30.9%) having the condition. Occupational stress was experienced by more pilots than non-pilots (45.5% vs. 27.3%, respectively). Bruxism was significantly associated with type of occupation (pilots vs. non-pilots) controlling for occupational stress in both univariate and multivariate logistic regression tests; odd ratio (OR) = 2.5; (95% confidence interval (CI): 1.1-5.4, p = 0.016) and OR = 2.6; (95% CI: 1.2-5.8, p= 0.020), respectively. Conclusions: The pilots demonstrated significantly higher occupational stress and bruxism than the non-pilots. The pilots were 3.9 times more likely to have a combination of stress and bruxism than non-pilots. Further investigations are necessary to determine whether any causal relationship exists between occupational stress and bruxism.