Material deprivation is an important determinant of health inequalities in adults but there remains debate about the extent of its importance for adolescent wellbeing. Research has found limited evidence for an association between adolescent health and socio-economic status, leading authors to suggest that there is an 'equalisation' of health across socio-economic groups during the adolescent stage of the life-course. This paper explores this 'equalisation' hypothesis for adolescent psychological wellbeing from a geographical perspective by investigating associations between neighbourhood deprivation and self-esteem in Britain and Canada. Data from the British Youth Panel (BYP) and the National Longitudinal Survey of Children and Youth (NLSCY) on adolescents aged 11-15 for the time period 1994-2004 were used to estimate variations in low self-esteem between neighbourhoods using multilevel logistic regression. Models were extended to estimate associations between self-esteem and neighbourhood deprivation before and after adjustment for individual and family level covariates. Moderation by age, sex, urban/rural status, household income and family structure was investigated. There were no significant differences in self-esteem between the most deprived and most affluent neighbourhoods (Canada unadjusted OR = 1.00, 95% CI 0.76, 1.33; Britain unadjusted OR = 1.25, 95% CI 0.74, 2.13). The prevalence of low self-esteem was higher (in Canada) for boys in the least deprived neighbourhoods compared to other neighbourhoods. No other interactions were observed. The results presented here offer some (limited) support for the socio-economic equalisation in youth hypothesis from a geographical perspective: with specific reference to equalisation of the relationship between neighbourhood deprivation and self-esteem and psychological health in early adolescence. This contrasts with previous research in the United States but supports related work from Britain. The lack of interactions with key social and economic variables suggests that findings might apply across a range of family circumstances and different communities in Britain and Canada. Policy implications are discussed.