Background: Breastfeeding is widely acknowledged as beneficial for both infant and maternal health. Maternal education significantly influences breastfeeding practices, which can, in turn, impact children's oral health outcomes. The purpose of this study was to explore the relationship between maternal education status and the duration of breastfeeding and its association with various oral health parameters in children aged 2–5 years. Methodology: The study employed a cross-sectional observational design, examining 188 dyads comprising mothers and their children. A structured questionnaire was employed to gather information on maternal education, breastfeeding practices, and demographic characteristics, which was subsequently complemented by an oral health assessment of the children. Primary outcome measures included breastfeeding duration and oral health parameters, such as dental caries, oral hygiene [assessed using the Simplified Oral Hygiene Index (OHI-S)], and malocclusions. Statistical analysis was performed using descriptive statistics, t-tests, analysis of variance, Chi-square tests, and multiple linear regression analysis to identify independent predictors of the outcomes. Results: Mothers with higher education breastfed for a significantly longer duration (mean: 11.8 ± 3.1 months) compared with those with lower education (mean: 8.4 ± 2.6 months) (p < 0.001). Children who were breastfed for 6 months or more had better oral hygiene scores (mean OHI-S: 1.5 ± 0.4) compared with those breastfed for less than 6 months (mean OHI-S: 2.1 ± 0.6) (p < 0.001). However, prolonged breastfeeding beyond 12 months was associated with an increased risk of malocclusions (χ² = 7.45, p = 0.006). Multiple linear regression analysis confirmed maternal education as a significant predictor of both breastfeeding duration (β = 0.42, p < 0.001) and oral hygiene status (β = −0.31, p = 0.002). Conclusion: This study highlights the significant role of maternal education in promoting longer breastfeeding duration and better oral health outcomes in children. However, extended nursing was associated with an increased risk of dental malocclusion. These findings highlight the importance of targeted community health programs focusing particularly on breastfeeding education and oral healthcare guidance, particularly for mothers with lower educational attainment.