Objectives: 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. Methods: 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. Results: 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). Conclusions: 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.