The goal was to identify perinatal predictors of early executive dysfunction in preschoolers born very low birth weight. Fifty-seven preschoolers completed 3 executive function tasks: Dimensional Change Card Sort-Separated (inhibition, working memory, and cognitive flexibility), Bear Dragon (inhibition and working memory), and Gift Delay Open (inhibition). Relationships between executive function and perinatal medical severity factors (gestational age, days on ventilation, size for gestational age, maternal steroids, and number of surgeries) and chronological age were investigated by multiple linear regression and logistic regression. Different perinatal medical severity factors were predictive of executive function tasks, with gestational age predicting Bear Dragon and Gift Open; and number of surgeries and maternal steroids predicting performance on Dimensional Change Card Sort-Separated. By understanding the relationship between perinatal medical severity factors and preschool executive outcomes, we can identify children at highest risk for future executive dysfunction, thereby focusing targeted early intervention services.