Aim: To investigate how changes occur in students’ health, self-esteem, and lifestyle habits according to grade progression. Method: A self-administered questionnaire survey of fourthto sixth-grade students from Prefecture X was conducted in December in 2010 and 2011. The survey included questions on the following: basic attributes, lifestyle habits (eating and sleeping habits), the psychosomatic complaints scale (hereinafter referred to as “PCs scale”), and the Self-Esteem Inventory (hereinafter referred to as “SEI”). Results: Data of 304 students for which the data matching between the 2010 and 2011 surveys was possible, were used for the analysis. The changes were examined between gender or grade, according to grade progression. Comparison of the 2010 and 2011 results showed that the prevalence of female students who ate breakfast daily significantly decreased from 87 fifth-grade students (94.6%) to 82 sixthgrade students (89.1%). The bedtime of male students changed significantly from 21:58 in the fifth grade to 22:28 in the sixth grade. This trend was also noted with female students whose bedtime changed from 21:55 in the fifth grade to 22:25 in the sixth grade. The length of sleep for female students shortened significantly from 8 h 28 min in the fifth grade to 7 h 57 min in the sixth grade. The PCs scale scores showed significant increase (p = 0.035) for female students from 28.0 in the fifthgrade to 31.4 in the sixth-grade. Within the subscales of SEI, there were no significant changes in any gender-grade groups. Conclusion: Skipping breakfast is considered a contributor to lifestyle-related diseases. Therefore, the results suggest the need for adequate health guidance that encourages improved breakfast habits for students. Maintaining a regular bedtime is one of the most important factors for a stable life rhythm, and the short length of sleep have negative impacts on health. Therefore, the results suggest the need to provide health guidance to fourthand fifth-grade students encouraging regular sleeping hours and bedtimes before 22:00. The fifth and sixth grades involve the period during which secondary sexual characteristics develop, and thus are characterized by considerable physical and psychological changes. The results suggest the importance of health support initiatives that help students resolve developmental issues of mind and body.