Gender dynamics are a complex yet interesting topic in the study of Cantonese opera, which has a rich heritage as a traditional art form in China. Gender representations in Cantonese opera often appear in differentiated forms, such as cross-dressing and cross-gender performances, and the common practice of male and female actors playing roles of the opposite gender. It is important to meticulously investigate the issues of gender representation and gender stereotyping when analyzing female roles in Cantonese opera. Traditional female roles often embody virtues such as being faithful, submissive, and chaste, while male roles are stereotyped as dominant, heroic, and wise. However, some contemporary productions challenge traditional gender roles (for example by including female leaders and warriors), with the aim of creating more varied and intricate characters and breaking away from over-emphasized gender stereotypes. In such cases, female roles can be depicted as self-determining and even resistant, while male roles can be more vulnerable and fainthearted. The gender boundary has been made more fluid by societal, cultural, and symbolic influences. Analyzing the metamorphosis of gender dynamics is critical in scrutinizing gender issues in Cantonese opera performances, which are multifaceted and evolving. In this chapter, female roles in Women Generals of the Yang Family, Liang Hongyu Beats the War Drum to Retreat the Jin Army, and Scent of a Lady are analyzed. The concepts of “progressive metamorphosis” and “impetuous metamorphosis” are introduced to show the essential differences between these characters and those in the traditional Cantonese opera plays The Flower Princess and The Legend of the Purple Hairpin.