Since the 1960's, the federal government has become increasingly more involved with the product of public education, tracking academic proficiency through the means of federally mandated high-stakes assessments (Ali & Favaro, 2007; Zumeta, 2011). Principal leadership is one of the most significant factors that can lead to academic proficiency, and has the potential to positively influence both teachers and students (Allen, Grigsby, & Peters, 2015; Corcoran, 2017; Jenkins et al., 2018). Although leadership has been identified as one of the most influential factors within the school setting, what type of leadership style would best benefit the diverse samples of school communities (Jenkins et al., 2018; Corcoran, 2017)? This study examined the relationship of Pennsylvania elementary schools' (grades 3-5) principals' transformational leadership style tendencies and the potential relationship between academic proficiency of the special education sample on the federally mandated Pennsylvania System School of Assessment (PSSA) exams using a non-experimental (simple case), quantitative survey. The sample for this study was 21 public elementary school principals serving in schools housing grades three through five, with a minimum of five years of experience in the role and currently acting as a principal in Pennsylvania. The results of this research study indicated that there was no statistical significance between the principals' transformational leadership style tendencies and this special education sample's academic achievement on the ELA, Math and Science PSSA exams. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]