Rates of victimization and bullying perpetration may vary by adolescents’ health status. The purpose of this study was to examine risk for bullying and victimization while considering multiple health conditions and health-related behaviors. Self-reported data were collected from 64,670 youth (50.3% female; 48.8% White; 25.7% Black/African American) enrolled at 107 middle and high schools across the state of Maryland. Two-level logistic regressions examined the association between health conditions and other health-related behaviors (i.e., physical activity, asthma, healthy eating, sleep troubles, obesity, and being overweight) and bullying. Results indicated that obese youth had higher odds of being a victim or bully-victim. Youth with asthma were more likely to be victimized, both in-person and online, and were more likely to be cyberbully-victims. Sleep difficulties were consistently associated with involvement in bullying, having higher odds of being a victim or bully-victim in-person and online as well as higher odds of perpetration of bullying. In contrast, healthy food consumption was associated with significantly lower odds of bullying perpetration, and physical activity was associated with significantly lower odds of being a bully-victim. Taken together, the findings suggest that various conditions and health-related behaviors may be important risk factors for both bullying victimization and perpetration.