The point of this article is to analyze the descriptions related to Japan in the first volume of Kansho-sho by Jikuun-Toren, which is now in the Kyoto University Library, and then to have a glimpse of the methodology of annotation on Chinese writings during the Muromachi Period. Jikuun's annotations strongly reflect his view of the contemporary social conditions and his eagerness to educate the coming generation. While thinking of the annotator's style in terms of the general way of annotating of the age, I will also consider why Kiyohara-Senken and his son transcribed the annotation and what the act of transcribing it meant to them.