This paper examines the process of translating Japanese texts with classical grammar into Chinese, focusing on two forms of Japanese literature: waka poetry and novels. By providing examples and analyses, the study explores the challenges of rendering Japanese classical grammar into Chinese under the guidance of Hans Vermeer's Skopos theory. It discusses translation strategies, stylistic choices, and the practical significance of these translations. The goal is to enhance readers’ interest and engagement with Japanese literary works, thereby deepening their understanding and appreciation of Japanese classical literature.