Objective: The aim was to assess subjective oral health symptoms and job stress, as measured by self-assessment of how demanding the job is, in male financial workers. Methods: The participants were recruited by applying screening procedures to a pool of Japanese registrants in an online database. For the stress check, 7 items about how demanding the job is were selected from The Brief Job Stress Questionnaire (BJSQ). Participants comprised a total of 950 financial male workers, ages 25 to 64. Results: Participants who answered "I can't complete my work in the required time" had more decayed teeth (p=0.010). Participants who felt that their job is highly demanding (answered affirmatively to 6 or all 7 items) were more likely to report "often get food stuck between teeth" (p=0.030), "there are some foods I can't eat" (p=0.005), "bad breath" (p=0.032), and "jaw makes clicking sound" (p=0.032). The independent variable of total stress score of 24–28 was found to be correlated to at least three oral health symptoms (OR: 3.25; 95%CI: 1.66–6.35). Conclusion: These results indicate that certain job stress factors are associated with certain oral health symptoms, and that oral health symptoms are likely predictors of job stress.