Round fan paintings of flowers and birds thrived in the Song Dynasty benefited from the prosperous in the fan-making industry and the prevalence of sketch painting across all social stratums. As people’s aesthetic standards improved, the designs of round fans diversified and the compositions of round fan paintings grew in variety, reflecting unique features of the time. This paper classifies the development of round fan paintings of flowers and birds in the Song Dynasty into three phases: early-Northern Song, mid- and late- Northern Song, and Southern Song, and discusses the evolutionary patterns and influencing factors of round fan paintings of flowers and birds in different stages. It is concluded that the Song Dynasty attained a high level of accomplishment in terms of the design and cultural connotations of round fan paintings of flowers and birds which had a profound influence on the development of such paintings thereafter.