Primary attachment relationships have an enormous influence on later cognitive development, socio-emotional development and psychological health. Up to date, no research explored the correlations between the quality of the child-caregiver attachment relationship (AQ), self-evaluation (SE), and cognitive development (CD) of five-year-old pre-school children. In accordance, the aim of this study was to explore the correlation between these three variables. Ten Afrikaans speaking mother-child dyads from white, two parent, first marriage families participated. Participants were assessed with the Pictorial Self-Evaluation Scale (PSES), The Observed Attachment Behavior Q-set (AQS), and The Griffiths Mental Development Scales; Extended Revised (GMDS-ER) in a single study in a South African context. Results indicate that a positive, medium to high practical significant correlations do exist between the reliabilities. However, because of the small number of infants tested, it was difficult in this initial sample to draw firm conclusions about the statistical significance of the results. Nonetheless the results obtained in this pilot study are very encouraging and holds great value for further investigation.