The evolution of classical Chinese poetry in Singapore is closely related to the immigration experience of Chinese intellectuals in various periods. The travelogues of the foreign trips by Chinese officials dispatched to Singapore in the late Qing dynasty, such as Zuo Binglong 左秉隆 and Huang Zunxian 黃遵憲, focused on the depiction of exotic landscapes and aimed to open up horizons. The poems written by Khoo Seok Wan 邱菽園 and Pan Shou 潘受, and numerous works published in local newspapers from the period before the Second World War to the 1970s, represented the highest achievement of characteristically classical Chinese poetry in Singapore. After the 1980s, the new type of poetry writing reflected in the "Xin Sheng Poetry Society" (Xin sheng shi she 新聲詩社) and poetic columns online was characterized by diversity in the path of communication and the choice of subject matter, as well as an overall decline in creative quality. This article attempts to present the different stages of classical Chinese poetry in Singapore and its features over the course of the century within the context of Sinophone literature.