This Singapore study involved a sample of 3776 secondary school students to examine the role of educational hope in moderating the relationships between teacher-student relationship dimensions (instrumental help, emotional support, relationship satisfaction, relationship conflict) and student engagement dimensions (perceived importance of schooling, school belonging, and effort expenditure). Besides its main associations with the student engagement dimensions, educational hope was found to be a significant moderator in the relationships (a) between perceived teacher instrumental help and perceived importance of schooling, and (b) between perceived teacher emotional support and effort expenditure, such that students high on perceived instrumental help or teacher emotional support and educational hope were also those high on the perceived importance of schooling or effort expenditure. This study demonstrates that the constructs, though theorised in Western contexts, have empirical utility and relevance for understanding the engagement of students in the Singapore context. Implications arising from this study are discussed.