This thesis critically explores: “Perspectives on the educational experiences of African Caribbean boys”. It draws upon the earlier literature in the field of secondary schools (Mac an Ghaill, 1988 and 1994, Gillborn, 1995, Sewell, 1997, Blair, 2001, LDA 2003). But this study adopts a comparative approach, specifically focusing on Black boys current experiences of both state secondary schooling and other areas of education, namely, a supplementary school and a youth organisation. Recent statistics have indicated a continuing high level of underachievement among African-Caribbean boys studying in British schools. The DFES 2006 reports that only 39% of Black pupils achieve 5+ A*-C GCSE grades which denotes that Black boys are among the lowest achievers at secondary school level as compared with pupils of other ethnic minority communities. The DFES further reports that Black pupils are more likely to be excluded from schools than pupils from any other group (Education and Skills, 2006). This study will go beyond the statistics by examining the reasons as to why Black boys have negative experiences in their secondary school education which is linked to their historically-based underachievement in secondary schools. The literature review of the study explores the academic literature/reports concerning African-Caribbean pupils’ underachievement (Mac an Ghaill, 1988, Wright, 1992, Benskin 1994, Gillborn, 1995, Sewell 1997, Ofsted, 1999, Blair 2001, LDA 2003, Education and Skills, 2006). The discussion reflects a number of inter-related issues that are shaped by the intersection of race, class and gender. These issues include: racialisation and accompanying negative stereotypes of the Black community and more specifically portraying Black masculinity as a problem, lack of respect for Black boys and their culture, peer group influence, and differences in treatment by teachers towards Black boys, as some of the significant factors affecting Black boys’ negative experiences at secondary schools and their resulting underachievement. In addition to examining the impact of these factors, as indicated above, this thesis critically examines two other areas of education, a supplementary school and a youth organization. Earlier studies have identified such sites as a powerful source of positive experiences for secondary school Black boys. This comparative, multidisciplinary approach enables original data to be gathered, in probing into the reasons as to why these institutions are successful in making Black boys educational experiences more meaningful. Over a course of six months, 36 participants were involved in this research study. The boys, their parents and their teachers were interviewed at the secondary and supplementary school. At the youth organisation, the Black boys and their youth workers were interviewed. The research used a wide range of methods, such as semi-structured interviews, participant-observation and non-participant-observation. This process provided the researcher with the bigger picture, giving insight into why Black boys have negative and positive experiences of education. The study makes a number of recommendations based on the findings, which include: actively recruiting more Black teachers to provide Black pupils with positive role models who understand their culture; employing Black culture/history in schools for the benefit of Black boys and teachers in state secondary schools learning from the other educational sites in terms of curriculum, pedagogy and relations between educators and Black male pupils. Such recommendations have been proposed in potentially being a step towards removing institutional racism within schools and promoting the career paths of these boys into successful professions.