This study focused on the peer and teacher relationships of deaf children and the effects of these relationships on well-being in school during the transition from elementary school to junior high school. Differences due to gender and educational context were also considered. In Study 1, the predictive effects of peer acceptance, popularity, and teacher support on well-being were examined cross-sectionally for early adolescents in Grade 6 (N = 759, 87 deaf) and Grade 7 (N = 840, 104 deaf). Study 2 examined the effects of the same predictors on well-being in school longitudinally during the transition to secondary school on a subsample of participants from Study 1 (n = 105). Well-being in school was stable during the transition for mainstreamed hearing children, but not for deaf children. In mainstream schools, school well-being increased for deaf boys but decreased for deaf girls. In contrast, in special education schools, school well-being increased for deaf girls but decreased for deaf boys. Peer acceptance, popularity, and relationship with the teacher had different effects on well-being for deaf early adolescents in mainstream schools compared to the effects on those in special education schools. Moderation by gender was also found.