Yunnanyuan yinchang ji (Correspondence Poems of the Yunnan Garden), Xingzhou gubao jiyoushi (Poems about the Excursion to the Old Fortress in Singapore) and Nanfeng ciji (Ci Lyrics of the Southern Breeze) are three classical poetry collections written by professors and students of the Chinese Department at the former Nanyang University in early 1960s. The first collection was produced to celebrate the first commencement of the university in 1960, when the Chinese Department invited many local poets for a celebratory feast, while the latter two are compilation of student assignments of poetry classes. This article first reviews the historical background of Nanyang University, which was seen as the champion of Chinese culture at the time when Singapore was troubled by racial politics and social disorder. The second part examines the compilation and content of these collections, offering some viewpoints about their cultural and literary significances in the history of classical poetry in Singapore. The author notes that the students who participated in the writing of these collections seemed to be aloof from the political tumult, fully emerging themselves in learning classical poetry and the beautiful scenery around the school campus. On the other hand the professors, who left China after the Communist takeover, adopted the yimin (people who remain loyal to the former regime, similar to loyalist) expression to manifest their nostalgia for the homeland. Among them, Liu Taixi played an instrumental role in promoting the art of classical poetry to the younger generations. Under his mentorship, students not only acquainted themselves with poetry, but also had the chance to take part in the literary activities of local poetry society. The author concludes that classical poetry writing had its heydays in Singapore before the decline of Chinese education, and its waning is as sad as the closure of Nanyang University.