Some researchers, including Wang Li 王力 (1900–1986) and Xu Qing 徐青 (1934–), have claimed—based on evidence provided by cursory observations of tonal arrangement—that pre-Yongming poets also attempted to create tonal contrast effects in pentasyllabic poems. In order to assess the validity of these claims, this study adopted a quantitative approach to the analysis of tonal contrasts in three early pentasyllabic poem collections: the “Nineteen Ancient Poems,” pentasyllabic poems written by Cao Zhi 曹植 (192–232), and pentasyllabic poems written by Xie Lingyun 謝靈運 (385–433). Unlike any previous study, the research presented in this article interprets tonal contrast data obtained in these poems in an enriched context. The author compares the tonal contrast rates in the poems written before the Yongming 永明 era (483–93) to tonal contrast rates obtained from narrative texts written in the same period, as well as to the ratios expected under the condition of random tonal arrangement. The results of these comparisons reveal that there is no simple answer to the question of whether tonal contrast existed in early pentasyllabic poems. Tonal contrast appears to have been in an intricate transitional stage that was likely initiated with an intuitive act of creativity rather than an intentional manipulation of tones to obtain a particular known effect.