Masaoka Shiki, who passed away at the age of 36, remained unmarried throughout his lifetime. What is interesting is that he described vividly many different types of women in his Chinese poems. However, while researching his works to find out how he regarded women is very important for our understanding of Masaoka Shiki’s poetry, earlier scholars did not pay any attention to it. For this reason, in this paper, I want to analyze the imaginary female figures and the realistic female figures in Shiki’s Chinese poems and try to figure out how Shiki’s view of female was.In the Meiji period, there was a unique family form in Japan, in which the first born son would be the householder and would have all the rights. Furthermore, Japan was still under the influence of Confucianism, the idea that men are superior to women was still prevalent. According to this historical background, Shiki should also has shared the Confucian idea of female. However, by reading his Chinese poems, we can realize that the Confucian idea of women cannot represent Shiki’s view completely. Quite the opposite, through Shiki's works, we can see that he was very considerate toward women. More specifically speaking, we can say that Shiki created several types of female figures in his works, specially in Chinese poems of sorrows and grievances（guiyuan）. There Shiki created four types of female figures: “the woman who is lonely”, “the woman who has a deep hatred”, “the woman who has consideration for her husband” and “the woman with a child”. He showed a conscious care for women and sent messages to himself in guiyuan poems. Apart from that, Shiki also created his ideal figure of prostitutes though his own experience and the ideal lover’s figure in his Chinese poems. From Shiki’s Chinese poems, we can also feel his deep affection for his mother and sister which had a huge influence on his opinions and attitude toward women, as for instance, those related to the necessity of female education and to his idea of free love and free marriage.