Given unique pathways contributing to hypertension among people with HIV, we sought to determine whether antihypertensive class was associated with cardiovascular disease (CVD) events among people with HIV. Among veterans with HIV and incident hypertension (2000–2018), we used propensity-score matching to evaluate risk of (1) incident/recurrent CVD or death, (2) incident CVD, and (3) incident heart failure by antihypertensive class. In supplementary analyses, we performed stratified analyses by race and chronic kidney disease status. Among 8041 veterans, 24% were initiated on ACE (angiotensin-converting enzyme) inhibitor/ARB (angiotensin receptor blocker) monotherapy, 23% on thiazide/thiazide-like diuretic monotherapy, 13% on β-blocker monotherapy, and 11% on calcium channel blocker monotherapy. Over a median of 6.5 years, 25% experienced a CVD event. β-blockers, but not calcium channel blockers or diuretics, were associated with an increased risk of incident CVD compared with ACEs/ARBs (hazard ratio [95% CI], β-blockers 1.90 [1.24–2.89]; calcium channel blockers 1.02 [0.77–1.34]; diuretics 1.06 [0.86–1.31]); similar hazard ratio were noted for incident/recurrent CVD or death. In veterans without chronic kidney disease, ACE inhibitor/ARBs were associated with a lower risk of incident heart failure compared with all other classes (hazard ratio [95% CI]: β-blockers, 1.52 [1.11–2.09]; calcium channel blockers 1.48 [1.00–2.19]; diuretics 1.52 [1.07–2.16]). In conclusion, we observed high rates of CVD events in people with HIV with hypertension and a high prevalence of β-blocker use for initial hypertension management, even among those without indications. Our findings highlight the potential harm associated with β-blockers and the possible benefit associated with ACE inhibitor/ARBs for hypertension management in people with HIV. Prospective and randomized trials are needed to confirm these findings.