Research suggests that encounters with racism are related to depression in Black youth. However, less is known about how experienced racial discrimination can influence other aspects of well-being among Black youth including their socio-emotional development and behavior. In addition, emerging literature highlights the critical ways anticipated racial discrimination may impact the emotional well-being of Black youth. To address these gaps, the current study assessed whether experienced discrimination was associated with higher levels of internalizing problems (anxiety/depression, suicidal thoughts) and lower levels of socio-emotional development (emotion regulation, prosocial behavior). We then tested whether expected discrimination contributed to similar patterns. Lastly, this study examined how age and gender moderated this relationship. Across eight schools in three communities, 1435 Black youth (56.57% female; 56.40% 10th grade) in 10th and 12th grades responded to the Youth Experience Survey. Using a series of hierarchical linear and hierarchical binary logistic regressions, results found that those who experienced racial discrimination and expected discrimination demonstrated higher internalizing problems and lower socio-emotional development; however, expected discrimination often accounted for more variance than experienced. These findings suggest the multifaceted influence both experienced and expected racial discrimination have on the well-being of Black youth and can provide important insights to community prevention systems.