This study compares the impact of two New York State mathematics Regents-level course sequences on the number of secondary mathematics courses taken by New York City Department of Education (NYCDOE) students and explores the potential that programming decisions could increase or diminish the mathematics learning opportunity and achievement of students in preparation for college and career. Schools programming practices vary in that some program all students for one sequence whereas other schools track students in mathematics by matching students to one of two secondary mathematics course sequences. A hierarchical generalized linear ordinal logit model was used to analyze NYCDOE student and school data due to the ordinal nature of the outcome variable. The sample used consisted of the cohort of NYCDOE students slated to graduate in the pre-pandemic 2018-19 academic school year. Deidentified student transcript and biographical data as well as publicly available school data were analyzed to determine the log-likelihood of students taking zero, one, two, three, or four standardized mathematics secondary courses, not including Algebra I. The findings revealed that 15% of students were highly likely to take three or more standardized mathematics courses while 85% of Cohort U students were highly likely to take two or fewer of the standardized mathematics courses, for which the content and rigor is known. Furthermore, schools' NYS Grade 8 Mathematics Test proficiency, affected the number of counted standardized mathematics courses likely taken by Cohort U students. For students attending schools that match students to one of two course sequences, the number of standardized courses that they were likely to take was negatively impacted. Black students attending schools identified as serving students with high economic need amplified the number of standardized secondary mathematics courses that they were likely to have taken by their expected graduation. For non-standardized alternative mathematics course, school or district-level ongoing assessment of content and rigor level is recommended to ensure adequate learning experiences in the absence of state, college, advanced placement, or international baccalaureate determined learning standards. Regarding the practice of matching students or tracking them for one of two programmed course sequences, it is recommended that school leaders ensure that the instruction provided to students taking either sequence is equitable and appropriate in content and rigor. Finally, policy changes pertaining to graduation requirements to prevent credit accumulation, not consistent with advancement in mathematics learning were recommended. [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.]