Despite evidence for executive dysfunction in school-aged preterm children, less is known about the early development of these difficulties or their underlying neuropathology. This study used prospective longitudinal data from a regional cohort of 88 very preterm and 98 full-term comparison children to examine the executive functioning (EF) of preschool children born very preterm. The relationship between the severity of neonatal cerebral white matter (WM) abnormalities on magnetic resonance imaging (MRI) at term equivalent and children's EF at ages two and four years (corrected age) was examined. At age four, very preterm children with WM abnormalities performed less well than full-term children on the Detour Reaching Box, a measure of behavioral inhibition and cognitive flexibility, even after controlling for child IQ, SES, and medical background. Examination of patterns of EF performance between the ages of 2 and 4 years showed that the performance of all groups improved with age. However, very preterm children with mild and moderate-severe WM abnormalities were characterized by higher rates of consistent performance impairments. These findings support the presence of early and persistent executive difficulties in preschool children born very preterm, and highlight the importance of white matter pathology in the development of executive impairments.