The current study aimed to address the gap in understanding how different types of race-related stressors (e.g., racial/ethnic (R/E) discrimination experiences and worries) are related to adolescents’ psychological adjustment (e.g., internalizing and externalizing symptoms) and further, how various sources of social support moderate the associations between race-related stressors on adolescents’ internalizing and externalizing symptoms. The sample included 835 adolescents, with 44% identifying as Black and 56% as Hispanic, with a mean age of 15.2 years old (SD = 1.58) (50.9% female; 49.1% male), drawn from a subset of the larger Project on Human Development in Chicago Neighborhoods (PHDCN) study. We ran descriptive statistics, correlations, and regression analyses using adolescent and parent-reported data. Results showed that R/E discrimination experiences were associated with both adolescents’ internalizing (p < 0.001) and externalizing symptoms (p < 0.001), whereas R/E discrimination worries were associated with only adolescent internalizing symptoms. (p < 0.01) There were no significant findings for the mitigating role of the different sources of social support on the relationship between R/E discrimination experiences and worries and adolescents’ internalizing and externalizing symptoms. However, supplementary analyses found that each source of social support had different significant direct effects on adolescents’ symptoms. The results highlight the intricate role of social support in response to R/E discrimination and adolescent psychological adjustment, emphasizing the need for targeted interventions that address specific support sources to effectively support adolescents.