The effects of the regular consumption of soy, barley, and green tea in a real-life setting are unclear. This longitudinal observational study showed the associations of their intake with cardiometabolic health when employees freely selected these foods in the workplace cafeteria of an industrial company in Japan. The consumption was objectively assessed by an electronic purchase system using integrated circuit chip-equipped tableware and personal identification cards. The associations between the cumulative number of servings of each food during the 12 weeks prior to a health examination and changes in cardiometabolic measurements were examined among Japanese male workers (n = 890). Higher total intake of soy products was associated with significant lower levels in low-density lipoprotein cholesterol. Higher total intake of rice with barley was marginally associated with lower levels in systolic blood pressure and glycated hemoglobin. These associations were attenuated after adjustment for the baseline values of the dependent variables. Serving soy and barley products in the workplace cafeteria possibly promotes real-life benefits to employees' cardiometabolic health.