Classical-style poetry in modern China and other Sinitic-speaking localities is attracting greater attention with the recent upsurge in academic revision of modern Chinese literary history. Using the concept of cultural transplantation, this monograph attempts to illustrate the uniqueness, compatibility, and adaptability of classical Chinese poetry in colonial Singapore as well as its sustained connections with literary tradition and homeland. It demonstrates how the reading of classical Chinese poetry can better our understanding of Singapore’s political, social, and cultural history, deepen knowledge of the transregional relationship between China and Nanyang, and fine-tune, redress, and enrich our perception of Singapore Chinese literature, Sinophone literature, the Chinese diaspora, and global Chinese identity.