The primary purpose of this paper is to examine the mutual relationship between school engagement of cross-border students (CBS) from Malaysia in Singapore and parental involvement in education. Focus-group interviews were conducted with school personnel, CBS and their non-local counterparts to provide a comprehensive understanding of the situation. The cross-border student group comprises diverse ethnicity and most of them are highly competitive and successful in engaging in the whole educational selection process from the beginning to their exit point. This paper argues that education for the CBS represents both a unique socio-cultural phenomenon in the two Asian societies and a manifestation of a widely shared pragmatic value of educational returns. The findings reveal that the nature of CBS engagement with schools is characterized by voluntary assimilation and is rewarded by the meritocratic system of Singapore.