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The risk of developing Type 2 Diabetes Mellitus in people living with HIV (PLWH) can be four times greater and can occur at an earlier age and even without the presence of obesity compared to those without HIV. Therefore, the purpose of this analytical cross-sectional study was to determine the relationship between HIV duration and glucose metabolism among PLWH. Eighty-two PLWH were categorized into shorter (≤15 years) or longer HIV duration (≥16 years) and then compared for differences in demographics, physical and clinical characteristics, biomarkers, and dietary intake. Compared to those with shorter HIV duration (n = 34), those with longer HIV duration (n = 48) were on average older (p = 0.02), reported lower consumption of alcohol (p = 0.05), had higher levels of homeostasis model assessment of insulin resistance (HOMA-IR, p = 0.02), were also more likely to be a woman (p = 0.06), and have higher levels of fasting insulin (p = 0.06). When adjusted for age and body weight, the levels of HOMA-IR and fasting insulin were higher (p = 0.02 and p = 0.04) with longer compared to shorter HIV duration, respectively. Longer exposure to HIV infection is associated with impaired insulin sensitivity. Continuing research aimed at the long-term effects of HIV infection and (antiretroviral therapy) is required.