The aim of the present systematic review and meta‐analysis was to evaluate the prevalence of dental caries among preschool children who had been born preterm and/or with low birth weight (LBW) compared with those who had been born full term and/or with normal birth weight (NBW). Eight electronic databases were searched from interception up to November 2018 with no restrictions imposed regarding the date of publication or language. Two independent reviewers screened studies, extracted data, and assessed the risk of bias. A random‐effects meta‐analysis was run to pool the crude prevalence of dental caries according to gestational age and birth weight. We performed a narrative synthesis and assessed the certainty of evidence using the Grading of Recommendations, Assessment, Development, and Evaluation (GRADE). Fifty‐nine observational studies were included (55 in the meta‐analysis). The prevalence of dental caries was 39% among preterm children, 30% among full‐term children, 40% among LBW children, and 33% among NBW children (I2:97%‐99%). The majority of studies reported that dental caries was not associated with gestational age or birth weight, with very low certainty of evidence. Preschool children born preterm or with LBW have similar dental caries experience as those born full term or with NBW, with very low certainty of evidence (PROSPERO #CDR42018118086).