Sugar-added diet has been associated with increased risk of developing dental caries. To investigate the dietary determinants of caries prevalence and experience based on the frequency versus the quantity of consumption among Saudi schoolchildren. This is a cross-sectional study that invited 12- to 15-year-old intermediate school students ( = 3000) in four cities in the Eastern Province of Saudi Arabia. Data collection comprised a pretested questionnaire and clinical examination. Caries was diagnosed based on the World Health Organization (WHO) criteria and was recorded as a decayed, missing, filled tooth (DMFT). The questionnaire included questions regarding the consumption of different quantities and frequencies of multiple sugar-containing food items. Multiple logistic and linear regression models were used to assess the influence of sugar-containing food on the dental caries experience (DMFT) and prevalence of decayed teeth. SPSS version 20.0 was used to analyze the data at 5% significance level. Of 3000 invited students, 2262 participated with a participation rate of 75.4%. Our study found that the frequency of soft drink consumption was significantly associated with increased caries prevalence (adjusted OR = 1.33, 95% CI 1.07-1.65) and experience (adjusted  = 0.46, 95% CI 0.16-0.76). The frequency of consumption of fruit juice was statistically significantly associated with increased caries experience (adjusted  = 0.48, 95% CI 0.16-0.79). The interaction terms between the frequency and the quantity of consumption of energy drinks, soft drinks, and sweetened milk were statistically significantly related to caries experience and prevalence. Although the frequency of consumption of sugar-containing drinks was more associated with caries experience and prevalence, the interaction between frequency and quantity was highly related to the prevalence and experience of dental caries.