Aspiration is increasingly recognized as a major risk for pneumonia, but a potential link between wearing dentures and incident pneumonia with aspiration risk is unclear. The aim of this study was to investigate whether denture wearing moderates the association between aspiration risk and incident pneumonia in older adults. We used prospective cohort data of 156 residents aged >70 years from eight nursing homes in Aso, Japan. Aspiration risk was evaluated using the modified water swallowing test. During a 1-year follow-up (2014 to 2015), information on incident pneumonia was obtained from nursing home medical records. During follow-up, pneumonia developed in 7.1% of participants. In the multivariate-adjusted Cox proportional hazards model, after adjusting for potential confounders, aspiration risk was independently associated with a 4.4-fold higher hazard ratio (HR) of incident pneumonia (95% confidence interval, CI, 1.16–16.43). The difference in the risk of incident pneumonia between subjects with aspiration risk who were wearing dentures and those not at risk of aspiration was not significant, whereas those with aspiration risk without dentures had a 7.3-fold higher HR of incident pneumonia than those not at risk of aspiration (95% CI, 1.02–52.63). Denture wearing might partially moderate the increased risk of incident pneumonia associated with aspiration risk.