This article analyzes how the structural factor of asymmetry affects China’s relations with a small power. As the studies of Brantly Womack suggest, asymmetry theory is conducive to deepening the understanding of China’s relations with smaller countries. We argue that an examination of China–Philippines relations from 2010 to 2020 indicates that Beijing has trouble managing its ties with Manila because of the asymmetry in the nature of the relations, which originates in the power and status gaps between them. The asymmetrical structure of this bilateral interplay inclines China to underestimate and neglect the Philippines’ intentions and determination to resist, which has been made especially clear in the South China Sea disputes. As a result, their relationship experienced repeated ups and downs throughout the 2010s, in particular over the maritime sovereignty issue. This study also hints at the complicated situations surrounding China where many medium-sized and small states attempt to maneuver among great powers. Without affinities with such governments in the Indo-Pacific region, it will be difficult for Beijing to achieve a peaceful rise and acquire status as a next-generation superpower.