Background and Purpose: Adolescence is a crucial period for developing healthy lifestyle and dietary habits. The growing consumption of high-sugar foods and beverages constitutes a serious public health concern. The aim of this study was to evaluate sex differences in the consumption of a sugary diet and oral health among Saudi adolescents. Subjects and Methods: This cross-sectional study was conducted in the Eastern Province of the Kingdom of Saudi Arabia between January and February 2019. A multistage sampling technique was used to recruit 2265 middle-school children aged 12-16 years. Data were collected via the Food Frequency Questionnaire and via an oral health examination, using the WHO criteria. The chi-squared test, Student's t-test, and Mann-Whitney U-test were used to investigate the associations between the study variables. Results: The most consumed foods and beverages reported were water, juices, and biscuits (90%), while the least consumed were energy drinks and jams. A significant difference was found between males and females in the frequency of consumed sugary foods (P=0.01) and the quantity of consumed sugary beverages (P=0.000); males over all consumption were greater than their counterpart. However, no differences were found between sexes in the frequency of sugary drink consumption (P=0.2). The decayed-missing-filled index score was significantly higher in females (4.29 ± 3.44) than in males (3.61 ± 3.14; P=0.001). The mean plaque index among males and females was 1.72 (±0.79) and 1.20 (±0.78), respectively, while the mean gingival index was 1.31 (±0.77) in males and 0.69 (±0.73) in females-a statistically significant difference (P=0.001). Conclusion: Sex differences were found in sugary diet consumption and oral health status. Thus, policy makers are encouraged to consider sex-based differences when planning preventative programs and initiatives. Nevertheless, further research is needed on the dietary intake patterns of young adults.