This retrospective qualitative research utilised ecological systems theory and content analysis to explore the pre-university experiences and barriers to participation faced by students with disabilities in Barbados and Trinidad. Findings suggested that attitudinal and environmental barriers heavily influenced the level of participation of students with disabilities at secondary school. In particular, the nature of social interactions in the micro and meso systems exerted a powerful influence on teacher-student and peers with and without disabilities' relationships. Teacher and peer interactions oscillated between being accommodating and conflictual. Implications suggest the need for more teacher training in inclusive practices and support to remediate dysfunctional relationships between students with disabilities, their teachers and peers at secondary school.