This study aimed to examine the association between both parental dental fear and children's dental fear and its impact on the Oral Health-Related Quality of Life (OHRQoL) of Saudi children in the Eastern Province of Saudi Arabia. Data on 93 individuals aged 7-12 years were collected using clinical examination and Arabic-validated questionnaires: the Child Oral Health Impact Profile-Short Form (COHIP-SF19), and the Children's Fear Survey Schedule-Dental Subscale (CFSS-DS). Negative binomial regression analysis was performed to study the association between children's fear and parental dental fear as well as the OHRQoL, while adjusting for certain confounders. Overall, our multivariate analyses showed that children with high dental fear (CFSS-DS ≥ 38, p = 0.027) and a higher percentage of dental caries (p = 0.013) had a significantly lower OHRQoL after adjusting for clinical and socio-demographic factors. Further, parental fear of dentists was significantly associated with children's fear of dentists (p < 0.001). Our findings demonstrate that children's fear and dental caries are both associated with poorer OHRQoL. Further, parental dental fear about dentists was associated with children's fear of dentists.