Fifty-seven percent of children with poor language skills are affected by socio-emotional problems. Despite the importance of language skills to interpersonal functioning and school performance, relatively little is known about how they affect self-esteem in adolescence. Data on youth at high risk for language problems (e.g. those born extremely low birth weight (ELBW; <1000 grams)) are even more scarce. This prospective study examined associations between language skills at age 8 and self-esteem during adolescence (12–16 years) in individuals born at ELBW ( N = 138) or normal birth weight (NBW; >2500 grams) ( N = 111). Participants’ language skills were assessed using the Verbal Scale of the Wechsler Intelligence Scale for Children-Revised and the Token Test at age 8. In adolescence, participants completed the Harter Self-Perception Profile for Adolescents. Birth weight status was found to moderate associations between childhood language and adolescent global self-esteem (Token Test ( p = .006), Verbal Intelligence Quotient ( p = .033)) such that better language skills were associated with higher self-esteem in adolescent ELBW survivors, but not in NBW participants. Language skills may play a protective role in the development and maintenance of self-esteem in ELBW youth and could be an important target for optimizing their functioning, particularly before transitioning to the critical adolescent period.