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This three-wave longitudinal study underscores the importance of identifying elements in school settings that can help academically at-risk students--those who are likely to follow a trajectory of low achievement or academic failure--to develop academic resilience. The study utilised both quantitative (ie, survey questionnaires and standardised achievement tests) and qualitative (ie, open-ended questions and semi-structured interviews) approaches, and focused on two subject domains--English Language (EL) and Mathematics (Maths). The participants of the study were 1305 students from 22 schools in Singapore. These students were considered as potentially at-risk academically as their aggregate scores in the Primary School Leaving Examination were lower than the cohort’s mean score. From this pool of students, students facing different levels of academic risk (ie, low, moderate and high) in EL or Maths were identified on the basis of their school grades and scores in standardised achievement tests at the end Secondary One (S1). Low language or numeracy proficiency on entry to secondary school, which is a critical transition phase in students’ life, was considered as a significant risk factor that can directly predispose students towards continued poor academic performance in later years.