To synthesise the current evidence for the associations between breastfeeding and dental caries, with respect to specific windows of early childhood caries risk. Systematic review, meta-analyses and narrative synthesis following searches of PubMed, CINAHL and EMBASE databases. Sixty-three papers included. Children exposed to longer versus shorter duration of breastfeeding up to age 12 months (more versus less breastfeeding), had a reduced risk of caries (OR 0.50; 95%CI 0.25, 0.99, I(2) 86.8%). Children breastfed >12 months had an increased risk of caries when compared with children breastfed <12 months (seven studies (OR 1.99; 1.35, 2.95, I(2) 69.3%). Amongst children breastfed >12 months, those fed nocturnally or more frequently had a further increased caries risk (five studies, OR 7.14; 3.14, 16.23, I(2) 77.1%). There was a lack of studies on children aged >12 months simultaneously assessing caries risk in breastfed, bottle-fed and children not bottle or breastfed, alongside specific breastfeeding practices, consuming sweet drinks and foods, and oral hygiene practices limiting our ability to tease out the risks attributable to each. Breastfeeding in infancy may protect against dental caries. Further research needed to understand the increased risk of caries in children breastfed after 12 months.