Children born very preterm (VPT) are at risk for academic, behavioral, and/or emotional problems. Mathematics is a particular weakness and better understanding of the relationship between preterm birth and early mathematics ability is needed, particularly as early as possible to aid in early intervention. Preschoolers born VPT (n = 58) and those born full term (FT; n = 29) were administered a large battery of measures within 6 months of beginning kindergarten. A multiple-mediation model was utilized to characterize the difference in skills underlying mathematics ability between groups. Children born VPT performed significantly worse than FT born children on a measure of mathematics ability as well as full scale IQ, verbal skills, visual-motor integration, phonological awareness, phonological working memory, motor skills, and executive functioning. Mathematics was significantly correlated with verbal skills, visual-motor integration, phonological processing, and motor skills across both groups. When entered into the mediation model, verbal skills, visual-motor integration, and phonological awareness were significant mediators of the group differences. This analysis provides insights into the pre-academic skills that are weak in preschoolers born very preterm and their relationship to mathematics. It is important to identify children who will have difficulties as early as possible, particularly for VPT children who are at higher risk for academic difficulties. Therefore, this model may be used in evaluating VPT children for emerging difficulties as well as an indicator that if other weaknesses are found, an assessment of mathematics should be conducted.