(1) Purpose: To assess the oral health literacy (OHL) of parents and its association with the caries experience of their preschool children attending the Hospital University Sains Malaysia (HUSM), Kota Bharu, Kelantan, Malaysia. (2) Materials and Methods: This is a descriptive cross-sectional study involving a systematic random sampling method, using a sample of 230 parent/preschool child dyads. Among 230 parents, 24 were males and 206 were females (mean age 31.43 ± 5.82); among 230 children, 92 were boys and 138 were girls (mean age 4.82 ± 1.04) attending the pedodontics clinic, HUSM, who participated and met the inclusion criteria. A structured, self-administered oral health literacy questionnaire including sociodemographic factors was used in this study. A child’s oral examination was performed to check the dmft (decayed, missing, filled teeth) status. Statistical analysis was done using descriptive and Spearman’s correlation analysis and multivariate regression analysis. (3) Results: The mean dmft score of children in relation to the OHL level of parents showed a significant difference (p
< 0.00). The mean dmft score of children in relation to the OHL level of parents showed the following relationships: Inadequate (7.49 ± 4.10) followed by marginal (3.28 ± 2.67) and then adequate (0.55 ± 1.55). The incidence of caries amongst children in relation to parental employment was more associated with unemployed parents (6.11 ± 4.43) than with employed parents (2.79 ± 3.65). The caries experience amongst children in relation to education of their parents revealed a significant difference (p
< 0.001), and the mean dmft score was high amongst preschool children with primary school qualified parents (10.7 ± 4.10) followed by high school (7.04 ± 3.68), vocational (5.81 ± 3.57), diploma (2.61 ± 2.81), and university (1.29 ± 2.27), respectively. The results revealed a valid significant difference (negative correlation, rs
= −0.753 **) between the OHL of parents with the dmft score of their preschool children. The age and gender of parents was not significantly associated with OHL, whereas ethnicity (positive correlation, rs
= 0.283 **), education (positive correlation, rs
= 0.865 **), and employment (negative correlation, rs
= −0.490 **) were found to be significant. Conclusion: We conclude that there is a significant association between the OHL of parents with the dmft score of their preschool children. The logistic regression showed that after adjustment for sociodemographic factors, parents’ gender (OR = 0.067, 95% CI: 0.012–0.360), parents’ employment status (OR = 3.247, 95% CI: 0.897–11.754), parents’ OHL score (OR = 0.042, 95% CI: 0.016–0.114), and child age (OR = 2.195, 95% CI: 1.249–3.857) were significantly associated with dental caries in children. Our study concluded that parents’ employment status, age, gender, OHL, and child’s age were significantly associated with the caries experience of their preschool children.