Objective The purpose of this study was to determine when dolichocephaly develops in preterm infants, to establish factors that contribute to its development, and to determine its association with adverse motor outcomes. Study Design This study was a retrospective review of data collected from preterm infants born at < 32 weeks' gestation. The cranial index was measured by a physical therapist (PT) at three time points during hospitalization. Demographic data, neonatal morbidities, and motor outcomes at outpatient follow-up were collected. Results Overall, 54% of infants developed dolichocephaly during hospitalization. The presence of dolichocephaly was highest in infants between 32 and 34 weeks' postmenstrual age (PMA) (39%). Birth weight, gestational age, bronchopulmonary dysplasia, gastroesophageal reflux disease, and severe intraventricular hemorrhage were not associated with dolichocephaly. Infants with dolichocephaly at 32 to 34 weeks' PMA were more likely to either be receiving PT services or be referred to PT services by outpatient follow-up (p = 0.05). Conclusion The presence of dolichocephaly was highest in infants between 32 and 34 weeks' PMA and was associated with increased need for PT services in early infancy. Findings support early developmental intervention at < 32 weeks' PMA to prevent and/or treat cranial molding deformity and improve early motor outcomes.