The primary objective of this study was to describe cognitive and pre-academic skills of children born preterm (< 30 weeks gestational age) at preschool age. A secondary objective was to relate cognitive functioning at preschool age to developmental scores obtained using the Bayley Scales of Infant and Toddler Development-Third Edition (Bayley III) administered at 18-28 months chronological age. Participants were 21 children born preterm who participated in an initial study and returned for follow-up assessment at 42-66 months. Measures administered at the preschool-age visit included the Differential Abilities Scale-2nd Edition (DAS-II) and the myIGDIs Early Literacy and Early Numeracy measures. Most children fell below benchmark standards for early literacy and numeracy skills on the myIGDIs at preschool age. Frequency of skill levels below benchmark varied from 65 to 95% for early literacy and 70-95% for early numeracy tasks. A subset of the children (n = 16) had Bayley III scores available from a research visit at 18-28 months corrected age. Among those, cognitive composite scores were associated with verbal, but not nonverbal reasoning on the DAS-II at preschool age, and only for those with significant delays on the Bayley III. Results indicated that at preschool age, children's average cognitive scores on the DAS-II were > 1 SD below the mean across verbal (SS = 82.67; SD = 23.76) and nonverbal (SS = 80.20; SD = 23.65) domains. Practical implications of early screening for specific academic skill difficulties in early childhood settings for children born preterm are presented.