This study investigates the influence of English language proficiency, academic stream, and digital skills on the higher education preferences and career aspirations of pre-university students in Sri Lanka. Using data mining techniques in WEKA 3.8.6, the Apriori, RandomTree, and REPTree algorithms were applied to identify correlations and predictors. Results revealed English proficiency and coding ability as dominant factors shaping students’ choices and opportunities. The findings emphasize the importance of enhancing digital literacy and language training to improve career equity. It offers actionable insights for educators and policymakers.