Background: Measuring oral health-related quality of life (OHRQoL) is a person-centered approach to investigating oral health. Proxy reports by parents or caregivers were used for assessing children's health-related quality of life (HRQoL) for decades. Using appropriate questionnaire techniques, it has become possible to get valid and reliable information from children about 8 years of age. Aims: The aim of the study was to investigate the OHRQoL of 8–10-year-old Libyan schoolchildren from viewpoints of both the children and their parents, in order to evaluate the concordance between child and parent ratings. Materials and Methods: This is a cross-sectional study using a representative sample of 303 8–10-year-old Libyan schoolchildren. Data were collected using Arabic versions of the Child Perception Questionnaire for 8–10-year-old children (CPQ8–10) and the Parent-caregiver Perception Questionnaire (P-CPQ8). Participants were examined for both traumatic dental injuries (TDI) and dental caries. Questions about the mother's and father's educational levels and current occupations were also asked, along with information on the child's age and sex. The collected data were analyzed using SPSS for Windows, version 25.0 (SPSS Inc., Chicago, USA). The alpha value was 0.05. Results: The mean CPQ8–10 score was 3.5 ± 4.2 (range: 0–18) overall, and those who had had caries experience or a TDI had higher CPQ8–10 scores, on average. The mean P-CPQ8 score was 7.5 ± 5.4 (range 0–27), and there were no apparent differences by parental education or employment status. The association between child and parental ratings of the children's OHRQoL was weak. The parents overestimated OHRQoL relative to their children's self-assessments. Conclusions: There is relatively low agreement between Libyan children and parents in their responses to OHRQoL scales, particularly in cases where that impact is greater. Where possible, if the aim is to obtain a more complete picture of the impact of a child's oral state on his/her life, both child and parental reports should be used.