This longitudinal study examined the relationship between executive function (EF) and mathematics with rural and urban preschool children. A panel of direct and indirect EF measures were used to compare how well individual measures, as well as analytic approaches, predicted both numeracy and geometry skill. One hundred eighteen children, ages 39 to 68 months, were given EF and mathematics assessments twice, approximately six months apart, concurrent to their teachers completing an indirect assessment of EF for each child. Results suggest: (1) the child's age determines if a panel of direct EF measures is a better predictor of numeracy and geometry skills than a single EF measure, (2) geometry and numeracy skill are influenced differently by contextual factors, and (3) the EF-geometry link may develop about six months later than the EF-numeracy connection. As the relationship between preschool age EF and mathematics is better understood, efforts can be made to improve the aspects of EF connected to mathematics skill, which may aid in performance.