This thesis is an examination of the sex and gender differences in measures of relative deprivation for Winnipeg, Manitoba, and the value of these measures to predict health outcomes. Within theoretical frameworks of relative deprivation and intersectionality, principal component analysis was used to test nineteen different versions of a national area-based deprivation index using Census variables, for the total population and for males and females separately. Only one version of the deprivation index provided consistent factor scores, in keeping with the theoretical constructs, for the total, female-only and male-only populations for Winnipeg. Administrative health data were used to calculate area-level rates of select health outcomes and binomial negative regressions were then used to analyze whether the “best” index was predictive of health outcomes for the three populations. In regression models, only the “material” component of the deprivation index was predictive of the health outcomes, but results varied across the three populations. The application of the “best” deprivation index to health planning may depend on the health issue and the population in question. This thesis confirmed that examining the intersections of sex, gender and deprivation in population health research unmasks important differences that would otherwise be missed and could have implications in health planning.