It is the aim of this paper to reconsider the origin and iconological evolution of the Water-Moon Avalokitesvara through an analysis of extant paintings as well as a study of related textual material. The earliest representation of the Water-Moon Avalokitesvara in the history of Chinese painting, is recorded to have been painted by Zhou Fang. On the other hand, the earliest extant sutra related to the Water-Moon Avalokitesvara (regarded to be an apocryphal work), the Shue Yue Guanyin Jing (or Sutra of the Water-Moon Avalokitesvara), was copied in 958 by Zhai Feng-da of Dunhuang in memory of his beloved wife. This sutra was copied from the Qienshou Qienyan Guanshiyin Psua guangda Yuanman Wu'ai Dabeixin Toloni Jing. From its earliest representation in the Shengguang Si at Chang'an, (see: Lidai Minghua Ji), through the mid-ninth century, the painting tradition of the Water-Moon Avaloktitesvara concentrated in Chang'an and spread as far west as Sichuan (see: Yizhou Minhua Lu), and east to Jiangxi province (see: Jo gyo kwu sho sho rai moku roku). Before the mid-tenth century, the tradition spread to Dunhuang area (see: wall-paintings form Dunhuang), and after the mid-tenth century, it was transmitted to Zhejiang province (see: Water-Moon Avalokitesvara from the objects in the inner chamber of Buddhist images of the Sakyamuni of Seiryo Ji). After the mid-eleventh century, paintings can be found in Fujian (see: Water-Moon Avalokitesvara in Besson zakki, plate 86). The evotution of representation of the Water-Moon Avalokitesvara appears to be closely related to the development of the Potalaka Mountain in China; at the same time, the development of landscape paintint during the Five Dynasties and the Northern and Southern Song, also exerted a stimulating influence on the evolution of representations of the Water-Moon Avalokitesvara. An analysis of the composition and structure of extant paintings furthermore shows how its image differs strongly from that of more traditional frontal Buddha and Boddhisattva representations, such as in the lotus position. The Water-Moon Avalokitesvara is mostly represented in a far freer, more unrestrained posture, which may even be called human-like in character. Images of nature such as the waterside, rocks, lotuses or bamboo, figure all among the defining iconological characteristics of representations of the Water-Moon Avalokitesvara.