This study critically explores contemporary African/Caribbean boys’ (15–16 years old) educational experiences in the UK. It focuses on their lives from both within and outside the school. Various research methods are employed in order to gain a comprehensive picture that includes the accounts of African/Caribbean boys, parents, teachers and youth workers. The study explores both the boys’ positive and negative experiences of school life. At one level, the boys’ narratives suggest ‘a nothing but the same old story’ of racial exclusion and subordination within urban secondary schools. At another level, we hear of the importance of education in their lives. Of particular significance is the evidence of how black supplementary schools and youth organisations are providing an educational space that positively supports them in their transition into adulthood. The study makes recommendations for educationalists and policy makers based on the findings. This includes the need to understand the boys’ experiences of racial exclusion and the complexities around the intersection of race, gender and class for a younger generation at the start of the twenty-first century. In comparing mainstream and supplementary educational spaces, the boys identify the need to build an inclusive mainstream curriculum that represents the historical past and cultural present of their lives. Importantly, the study vividly highlights contrasting teacher-pupil interactions between these two educational spaces, suggesting what the former can learn from the latter.