This study used the diary data from 5 people - Den Kenjirō, Utsumi Chūji, Lin Hsien-tang, Zhang Li-Jyun, Huang Wang-cheng, whose identity was governor, Chiji, gentry, Bao Chief and teacher of public school, respectively, to analyze the records of sports activities that the Taiwanese of different social backgrounds were exposed to in their daily life, in order to investigate the development of sports history in Taiwan during the period of Japanese ruling. The diary of Den Kenjirō showed that he enjoyed playing tennis, and playing tennis was one of activities for family gatherings and social interactions. He also frequently inspected the sports meets held everywhere. During the reception of the imperial family of Japan, he often scheduled for sports activities. Utsumi Chūji had served as the police chief and administrative director in various places in the northern, central and southern Taiwan. He personally enjoyed riding horses and playing golf. He recorded the information on golfers and the establishment of golf courses at various places in his diary. Lin Hsien-tang was a leader in the society in Taiwan at the time, and was personally good at various sports. He also had convened local sports meets. Zhang Li-Jyun served as the Bao Chief in Fengyuan for a long period of time, and also had participated in the operation of Dai Nippon Butoku Kai and local sports meets. Huang Wang-cheng served as the teacher in public school in Hsinchu in his early years. He directly and explicitly recorded the sports meets held at school and the leisure sports of tennis. This study investigated the sports history in Taiwan during the period of Japanese ruling mainly based on the sports activities that the senior government officers in the colonial government and Taiwanese elites had personally participated in. Although several prior studies have been conducted, diaries were seldom used as main research materials. It is hoped that this study may provide a different research approach for the investigation on sports history in Taiwan during the period of Japanese ruling.