In the past two decades, young women’s educational performance in Hong Kong has gradually improved; yet this has sparked concern over boys’ “under-achievement.” Despite prevalent concern, however, few academic studies have seriously considered this complex phenomenon. Inspired by feminist discussions on this topic, this chapter explores the contradictory construction of successful female leaders in an elite girls’ school in Hong Kong. The discussion aims to show that the discourse and expectations of “successful girls” are similar to those in Anglophone countries and that they are intimately linked to Hong Kong’s neoliberal educational reforms, middle-class oriented, and fraught with contradictions.