The aim of our study was twofold: to examine (a) whether the link between racial discrimination and adjustment showed age-related changes across early to late adolescence for Chinese-heritage youth and (b) whether the age-related associations of the discrimination–adjustment link differed by gender, nativity, and geographical region. We pooled two independently collected longitudinal data sets in the United States and Canada (N = 498, ages 12–19 at Wave 1) and used time-varying effect modeling to show that discrimination is consistently associated with poorer adjustment across all ages. These associations were stronger at certain ages, but for males and females, first- and second-generation adolescents, and US and Canadian adolescents they differed. There were stronger relations between discrimination and adjustment in early adolescence for males compared to females, in middle adolescence for first-generation compared to second-generation adolescents, and in early adolescence for US adolescents compared to Canadian adolescents. In general, negative implications for adjustment associated with discrimination diminished across the span of adolescence for females, second-generation, and US and Canadian adolescents, but not for males or first-generation adolescents. The results show that the discrimination–adjustment link must be considered with regard to age, gender, nativity, and region, and that attention to discrimination in early adolescence may be especially important.