AIDS has increased the number of orphans and vulnerable children (OVCs) in sub-Saharan Africa who could suffer detrimental life experiences. We investigated whether OVCs have heightened risks of adverse reproductive health outcomes including HIV infection. Data on HIV infection, sexually transmitted infection (STI) symptoms and pregnancy, and common risk factors were collected for OVCs and non-OVCs in a population survey of 1523 teenage children in eastern Zimbabwe between July 2001 and March 2003. Multivariate logistic regression was used to test for statistical association between OVC status, adverse reproductive health outcomes and suspected risk factors. Amongst women aged 15-18 years, OVCs had higher HIV prevalence than non-OVCs (3.2% versus 0.0%; p = 0.002) and more common experience of STI symptoms (5.9% versus 3.3%; adjusted odds ratio = 1.75, 95% CI 0.80-3.80) and teenage pregnancy (8.3% versus 1.9%; 4.25, 1.58-11.42). OVCs (overall), maternal orphans and young women with an infected parent were more likely to have received no secondary school education and to have started sex and married, which, in turn, were associated with poor reproductive health. Amongst men aged 17-18 years, OVC status was not associated with HIV infection (0.5% versus 0.0%; p = 1.000) or STI symptoms (2.7% versus 1.6%; p = 0.529). No association was found between history of medical injections and HIV risk amongst teenage women and men. High proportions of HIV infections, STIs and pregnancies among teenage girls in eastern Zimbabwe can be attributed to maternal orphanhood and parental HIV. Many of these could be averted through further female secondary school education. Predicted substantial expanded increases in orphanhood could hamper efforts to slow the acquisition of HIV infection in successive generations of young adults, perpetuating the vicious cycle of poverty and disease.