The achievement gap is a topic that has plagued the education research field for a long time. This persistent quandary is often rooted in disparities along racial, socioeconomic, and other demographic lines, such as geographical location. This study focuses on the achievement gap within the context of the Mississippi Delta. This rural region of the American South is plagued by a variety of social demographic factors that affect student educational success. To evaluate the impact of contextual and demographic factors on student achievement in the Mississippi Delta, this study analyzes test scores from a sample of districts within the Delta and compares them to test scores from districts outside the Delta region. The analysis covers school years from 2018-2019 to 2021-2022, including both pre- and post-pandemic periods. The study examines all 30 school districts in the Mississippi Delta region and randomly selects a control group of 28 school districts from outside the Delta for comparison. The study primarily uses hierarchical linear regression to ascertain the extent and nature of the association between district-level academic outcomes, while controlling for various independent variables such as neighborhood characteristics and financial variables. Through the lens of critical geography, this study delineates how much context matters in terms of educational achievement, or the lack thereof. The research data are sourced from the Common Core of Data, the Stanford Education Data Archive, the American Community Survey (U.S. Census Bureau), and the School Finance Indicators Database. The findings of this study indicate that the Delta status of a school district exhibits a negative relationship with average achievement across all outcome variables. However, Delta districts show a more pronounced increase in average achievement with each additional percentage of the white population in the neighborhood. Accounting for per pupil expenditure, findings show that money does not have a statistically significant impact on educational achievement. These findings underscore the need for policy-inclined implications such as better investment in school funds in order to provide the Delta Districts with research-proven action items such as smaller class sizes, better teacher development, parent efficacy resources, and better curriculum, amongst other educational resources. [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.]