As children enter kindergarten, some are more academically prepared than others for a variety of reasons. One influence on kindergarten preparation is prior preschool experiences. The purpose of this study was to investigate the relationship between children’s mathematical literacy at kindergarten entry and preschool attendance, preschool type (i.e., public, private, Head Start, and home-based educational technology providers), and preschool quality. Researchers collected statewide preschool enrollment records and kindergarten-entry mathematical literacy assessment scores for 45,895 public school kindergarten children for one school year. To identify relationships between early mathematical literacy performance and children’s preschool attendance, preschool type, and preschool quality, researchers conducted a 2 × 2 Factor ANOVA, independent group means t-tests, and multiple regression analyses. Overall, the results suggested that children from diverse backgrounds experience improved early mathematical literacy when they attended preschool. Therefore, with the limited funding available for preschool, policymakers should consider which children might most benefit from preschool experience and target limited resources to such populations.