In the United States, when a child turns five years of age, he or she is eligible to enroll and attend five-year old kindergarten. Parents and caregivers are often tasked with making the decision on whether or not to enroll their child when eligible to attend kindergarten or if the child should be held back another year (redshirted) and attend kindergarten the following year, thus allowing the child to be older. The purpose of this quantitative study was to examine the relationship between a child's age when beginning kindergarten and his or her academic outcomes, utilizing variables from within data that already existed, the Early Childhood Longitudinal Studies Program: Kindergarten: 2011. Of the 20,000 children within the dataset, the sample size consisted of approximately 13,380 children all with diverse socio-economic backgrounds, ethnicities, gender, and geographical locations. Through multiple regression analyses, it was determined that students who were red-shirted did better than those who were not redshirted in both reading and mathematics to some ex-tent. Further examination determined that in both kindergarten and second grade, students who were redshirted did significantly better than their peers in both reading and math. In first grade, those who were redshirted did significantly better in mathematics. In grades third through fifth students who were redshirted did not do better based on the standardized assessments in reading and mathematics. The results of this study should be important to policy makers, administrators, educators, and parents/families as they review the demands and expectations placed upon children entering kindergarten. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]