Older adults participating in Masters sport have often been promoted as an ideal model of successful aging. As a result, Masters athletes are a particularly interesting group to investigate issues of aging, due to their continued participation in higher than average levels of physical activity and competitive sport. Researchers have also highlighted the benefits of participating in cognitively engaging activities (e.g., chess, crosswords). A key constraint of involvement in sport and physical activity is presence of chronic conditions or injuries, which is paradoxical since involvement in physical activity is a key preventive strategy for mitigating chronic disease risk. The current study explored the rates and types of physical injuries and chronic conditions experienced in Master Athletes (n=106) and Chess players (n=42), as well as the Canadian normative data for moderately-active adults (n=2647), and sedentary adults (n=5154). All groups included participants aged 50 years and above. Preliminary results suggest Masters athletes experienced significantly higher rates of all injuries (M=1.14, SD=1.2) in conjunction with a decreased prevalence of chronic conditions compared to chess players (M=0.14, SD=0.44), inactive (M=0.12, SD=0.39) and moderately active (M=0.13, SD=0.40). Chess players were significantly less likely to experience chronic conditions compared to the moderately-active and inactive group (OR:8.98 CI:4.38-18.41; OR:10.89 CI:5.33-22.27); however, they were not significantly different from Master athletes. These findings expand our knowledge on the health status of older adults who are Master sport or chess participants, and have implications for promoting both physically- and cognitively-engaging leisure activities for aging cohorts.