•Internalizing symptoms in preterm and term preschoolers were assessed from four perspectives.•From the parents’ perspective, higher levels of internalizing symptoms were found in preterm children.•From the teacher's and the child's own perspective, the group differences were not significant.•Parental postpartum psychological distress predicted higher levels of children´s internalizing symptoms.•Prematurity did not predict internalizing symptoms from any of the four perspectives. Preterm births rates of infants with very low birth weight (VLBW < 1500 g) are increasing. Prematurity poses several risks for emotional child development, e.g., internalizing symptoms. Our understanding of this condition in young children is limited, for at preschool age, symptoms have mostly been assessed from the mother's perspective only. As part of the longitudinal HaFEn cohort-study in Hamburg, Germany, we measured the level of internalizing symptoms in VLBW and term preschoolers as well as predictors from four informants’ perspectives: mother, father, teacher, and child. A multilevel model was constructed to examine predictors of internalizing symptoms. n = 104 VLBW and n = 79 term children were included. From both their parents’ perspective, children with VLBW had a significantly higher level of internalizing symptoms. From the teacher's and child's own perspectives, there were no significant mean group differences. In the multilevel analyses, the results were different regarding the four perspectives. VLBW did not predict internalizing symptoms. From mother's perspective, her own postpartum psychological distress, and from father's perspective, his postpartum and current psychological distress predicted a higher level of internalizing symptoms in their offspring. From teacher's perspective, socio-economic status predicted internalizing symptoms. The sample size was relatively small. Exclusion criteria and drop out of families could have created some selection bias. Our findings point to the importance of early identification of parental postpartum psychological distress given the potential for later internalizing symptoms in their children or the perception of their offspring as vulnerable and symptomatic, which may also impact the child's development.