The relationship between self-regulation and achievement has been identified. The literature suggests, students with high levels of self-regulation have higher academic achievement. However, less is known about gifted students’ self-regulation, although it is widely accepted that underachievement is an issue facing the gifted school-aged population (National Association for Gifted Children (NAGC), 2000). Underachievement is a problem and self-regulation and underachievement are related (Stoeger & Ziegler, 2005). Self-regulation studies have been inconsistent in that higher levels of self-regulation and lower levels of self-regulation among gifted students have been reported (Stoeger & Ziegler, 2005). A number of studies have examined self-regulation in the gifted adolescent population few have examined the preadolescent population. Most studies compare levels of self-regulation in gifted students to their non-gifted counterparts. In an attempt to broaden the research on self-regulation in gifted students, this study investigated underachievement in preadolescent gifted students receiving special education services in public schools while regarding potential predictor variables gender and self-regulation. Survey data were collected from 114 gifted students in Grades 4 to 6 and their teachers in two different school districts. The study used the School Attitude Assessment Revised (SAAS-R) (McCoach & Seigle, 2003) and the Comprehensive Executive Functioning Inventory (CEFI) (Naglieri & Goldstein, 2013). The SAAS-R measures students’ attitudes toward school/teachers, goal valuation, motivation/self-regulation, and general academic self-perceptions. The CEFI measures the level of executive functioning across nine subscales: attention, emotional regulation, flexibility, inhibitory control, initiation, organization, planning, self-monitoring, and working memory. No significant differences were found between race and gender on the dependent variable of self-regulation indicating the effects of self-regulation are dissimilar based on race and gender. The regression models yielded significant results on the predictors reading and math achievement. Reading and math achievement significantly predicted self-regulation. There was not a significant difference on reported levels of self-regulation based on grade level. Implications from this study suggest that practitioners should consider the impact of self-regulation on achievement and implement strategies to enhance self-regulation in the classroom. Additionally, gender, grade level, and racial difference in achievement and self-regulation should be acknowledged and factors to remediate them should be implemented.