Culturally proficient school leadership and its impact on narrowing the learning gap is both timely, and needed and the focus of discussion for this study. This phenomenological qualitative research study examined culturally proficient school leadership actions that help promote a measurable narrowing of the achievement gap in five southeastern Wisconsin urban schools. The researcher examined the belief that if a leader promotes and establishes the conditions for cultural proficiency, children of color will benefit, and academic outcomes will increase hence, a narrowing of the learning gap will be evident. The participants in this study were selected on the basis of 25% enrollment of minority population and their districts accountability results as measured through state and federal testing requirements. Each school district leader chosen marked improvements in closing the learning gap (the difference between percentage of minority students passing the state accountability test and the majority [White] students) during the same time period as documented through the WKCE test scores. Qualitative data was collected through structured in-depth interviews with five elementary school principals to examine culturally proficient beliefs and practices. Eight themes emerged from this descriptive case study that included: Achievement Gap & Leaders Role, Teacher Preparation, Values & Beliefs, Relationships, Honor & Respect, Courage & Change, Assumptions & Stereotyping and Expectations. The conclusions were significant and reflected in the learning gap being narrowed for students of color and that culturally proficient school leadership practices can impact the learning gap. [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.]