Increasingly over the past decade, research has sought to describe and better understand patterns of engagement in the continuum of health care services for people living with human immunodeficiency virus (HIV), and to identify factors that shape engagement. The HIV care cascade was developed as a framework to examine and monitor engagement across sequential stages of the continuum of HIV care, from HIV acquisition to virologic suppression. In Manitoba, data describing the epidemiological trends of HIV and the delivery and utilization of relevant services is scarce. As a result, local understandings of engagement in HIV care are limited. Together, the three studies compiled in this dissertation offer a foundation upon which to expand upon and provide nuance to our current knowledge of HIV epidemiology and HIV-related service coverage in Manitoba. This was specifically achieved through the expansion of local data infrastructure for doing HIV research and programming and the use of an HIV care cascade framework to better conceptualize and understand HIV clinical epidemiology and related health services within the province. First, this work describes the establishment of the first prospective clinical cohort of people living with HIV and receiving HIV care in Manitoba, which was strategically created as an embedded research component of the Manitoba HIV Program. Individual-level clinical data from cohort participants are anonymously linked to relevant provincial administrative health databases. Using these linked data, multiple sets of HIV care cascade indicator definitions were developed through an iterative consultation process with local experts in HIV care, resulting in a final cascade model including the most programmatically relevant indicator definitions and locally relevant estimates. Finally, equity analyses were performed using care cascade data, disaggregated by key demographic and socioeconomic variables. Equiplots were used to visualize absolute inequalities among groups of cohort participants across the cascade steps and multivariable logistic regression models assessed statistical significance of observed inequalities. Expanding local data infrastructure through the development of the first clinical cohort of people living with HIV in Manitoba afforded important opportunities for addressing critical research, programming, and policy questions. Using cohort data to develop a locally relevant HIV care cascade model revealed promising patterns of engagement in HIV care in the province, while highlighting key points of disengagement across the cascade. In particular, individuals living with HIV who are younger, non-white, or have a history of injecting drugs are less likely to be optimally engaged in care in Manitoba. Together, the bodies of work in this dissertation generated evidence, knowledge, and specific tools that can be used to further our understanding of the most effective ways to optimize coverage of HIV care in Manitoba and work towards achieving equity in the health and well-being of people living with HIV in the province.