The goals of the current study were to (1) examine differences in pragmatic abilities and peer relationship behaviors among deaf and hard of hearing (DHH) adolescents who use spoken language, in comparison with their hearing peers; and (2) explore the contribution of pragmatic skills and speech (ie, articulation and intelligibility [AI]) to social aspects of school functioning among DHH and typically hearing adolescents. Thirty-three DHH adolescents and 34 adolescents with typical hearing participated. All DHH adolescents attended mainstream school settings and used spoken language. Teacher reports were obtained on prosocial behaviors, peer problems, pragmatic abilities, and speech AI of the adolescents. Adolescents self-reported on the supportiveness of their peer relationships and their school emotional engagement. Multiple hierarchical regression analyses revealed that DHH adolescents had greater difficulties with peers than their hearing counterparts. Increased pragmatic difficulties were related to more peer problems and decreased prosocial behaviors, regardless of adolescents' hearing status. A significant positive correlation was found between pragmatic competence and adolescents' perceptions of peers' support. Finally, better speech AI were associated with higher levels of school emotional engagement. The results emphasize the significant role of pragmatics for both DHH and typically hearing adolescents. Medical care providers and allied health professionals should be aware of possible difficulties that DHH adolescents may have in complex and nuanced pragmatic skills. Some adolescents may require a referral to specialized services to support the development of their pragmatic understanding and their skills.