Although HIV is more prevalent among transgender and gender-diverse individuals than cisgender people, a dearth of research has compared the HIV-related care engagement of these populations. Using 2008-2017 Medicare data, we identified TGD (trans feminine and non-binary [TFN], trans masculine and non-binary [TMN], unclassified gender) and cisgender (male, female) beneficiaries with HIV and explored within and between gender group differences in the predicted probability of engagement in the HIV Care Continuum. Transgender and gender-diverse individuals had a higher predicted probability of every HIV-related care outcome vs. cisgender individuals, with TFN individuals showing the highest probability of HIV care visit engagement, sexually transmitted infection screening, and antiretroviral treatment receipt and persistence. Notably, except for sexually transmitted infection screening, cisgender females and TMN people had a slightly lower probability of engaging in HIV-related care than TFN people and cisgender males. Although transgender and gender-diverse beneficiaries living with HIV had better engagement in the HIV Care Continuum than cisgender individuals, findings highlight disparities in engagement for TMN individuals and cisgender females, though engagement was still low for Medicare beneficiaries of all genders. Interventions are needed to reduce HIV care engagement barriers for all Medicare beneficiaries.