Rates of osteoporosis and fracture may be increased in HIV but there are few UK data. Our aim was to examine the prevalence of and risk factors for osteoporosis and fractures among a homogeneous cohort of well-characterized HIV-infected men. In total, 168 men were recruited, median age 45 years, 37 combined antiretroviral therapy naïve, 46 with <3 years combined antiretroviral therapy exposure and 85 combined antiretroviral therapy exposed longer term (median >10 years). All participants provided information on bone health and underwent DEXA scanning. Osteopenia was found in 58% of subjects and osteoporosis in 12%; 14% reported fractures since HIV diagnosis. Number of fractures since HIV diagnosis was significantly increased amongst those with osteoporosis (OR 3.5, 95% CI 1.2–10.4, p = 0.018). Duration of infection greater than 13 years was significantly associated with osteoporosis. Duration of combined antiretroviral therapy was associated in univariate and not multivariate analyses. Strategies to prevent osteoporosis and fractures in HIV will require attention to viral and lifestyle factors and not just combined antiretroviral therapy.