Male students appear not ready for middle school by exhibiting lower grades, learner disengagement, and/or behavior problems. The age in which male students initially enter school has not been fully investigated as a possible systemic issue of a lack of male student longitudinal success and learner engagement. The purpose of this quantitative study was to examine the differences between how academically redshirted male students performed academically and behaviorally compared to their non-academically redshirted grade mates at Grades 6-8. This study drew from the theories of early childhood constructivists: Piaget, Vygotsky, and Montessori. The research questions addressed the academic and behavioral differences between redshirted and non-academically redshirted students throughout Grades 6-8. Academic data, through numerical average and GPA, and behavioral data, through the total number of behavioral violations, from 1 archived school year were gathered for all male students in grades 6-8 (N=109). Students were grouped academically redshirted or non-academically redshirted based on age of school entry. A series of independent t tests were performed on all academic and behavioral data for each of the respective grades and sets of student data. Findings revealed differences in how redshirted versus non-academically redshirted students performed; however, these findings revealed no statistically significant difference. The results of this study provided evidence to support a correlation between when male students formally enter school and male academic and behavioral success. These findings lead to positive social change for school communities, specifically parents/guardians and school officials, by providing necessary data to drive decisions regarding school entry age and its longitudinal effects at the middle school level.