Objectives: This retrospective cohort study evaluated the impact of the Stress Check Program, a recently introduced national policy and program aimed at reducing psychological distress among Japanese workers. Methods: A baseline survey was conducted from November 2015 to February 2016, the period when Japan began enforcing the Stress Check Program. A one-year follow-up survey was conducted in December 2016. In the follow-up survey, two exposure variables were collected: having taken the annual stress survey, and experiencing an improvement in the psychosocial work environment. Psychological distress was assessed using the Brief Job Stress Questionnaire (BJSQ) at baseline and 1-year follow-up. The two exposure variables were used to define four groups: "Neither", "Stress survey (SS) only", "Psychosocial work environment improvement (WI) only", and "Both". BJSQ results were analyzed using repeated measures general linear modeling (GLM). Results: The study included 2,492 participants: 1,342 in the "Neither" group, 1,009 in the "SS only" group, 76 in the "WI only" group, and 65 in the "Both" group. Overall time-group interaction effects were not significant. The "Both" group showed significantly greater improvements in psychological distress than the "Neither" group ( p = 0.02) at the 1-year follow-up, although the effect size was small (d = -0.14). Conclusions: Combination of the annual stress survey and improvement in psychosocial work environment may have been effective in reducing psychological distress in workers, although the effect size was small.