Sesshu Toyo (1420-1506) was a preeminent Japanese monk painter who journeyed to China in the mid-fifteenth century. This thesis focuses on a diptych of landscape paintings by Sesshu Toyo, Autumn and Winter Landscapes (Shutou sansui zu), to analyze how Sesshu; selectively synthesized traditions of Chinese painting tradition that had already been established in Japan and the art conventions he discovered in fifteenth-century China. To contextualize this topic, this thesis explores the revival of the Southern Song (1127-1279) painting tradition which had impacts on both contemporary Chinese painters and landscape painters in Japan during the fifteenth century. I also analyze the culture of Japanese Zen monastics and their art-related activities and the transformation of Southern Song painting traditions within China in the early Ming period (later half of the fourteenth century-first half of the fifteenth century).