Vaginal rings have recently become attractive drug delivery systems for the prophylactic prevention of sexually transmitted HIV infection. Delivery of a single anti-HIV drug has been shown to promote drug-resistant HIV strains, resulting in ineffective prevention against HIV. As a result, we have developed a monolithic polyurethane vaginal ring for the dual delivery of anti-HIV drugs Dapivirine and Tenofovir to combat the major problem of drug-resistant HIV. We have demonstrated near-linear release of both Dapivirine and Tenofovir from rings submerged in a vaginal fluid simulant over 30 days. Furthermore, both drugs were released from the polymer in a loading-dependent manner, suggesting that release can be tailored to suit the clinical efficacy of the drugs. Dapivirine and Tenofovir were also found to be stable in the polymer matrix at an elevated temperature for 30 days. Lastly, mechanical testing was performed to compare the device to Nuvaring, a contraceptive ring that has shown excellent user acceptability, and thus serves as a benchmark for mechanical characterization for our ring.