A wealth of literature on gender identities undertaken by western research communities shows that gender scripts have real consequences for male and female teachers' identity constructions. Social expectations and stereotyped images of men and women teachers affect teachers' gender identities as well as their professional experiences and opportunities (Biklen, 1995; Casey, 1990; Coffey & Delamont, 2000; Smedley, 2007; Tamboukou, 2000; Wayne & Blye, 2006). There has been growing research efforts into research on Chinese women primary teachers (Chan, 2004; Luk-Fong, 2010). Little published work on Hong Kong Chinese men and women secondary teachers have been found. Understanding teachers' gender identity is important because the way gender dynamics has worked to shape teachers' gender identities in their school days may field results for the students they interact with. Sabbe and Aelterman (2007), in their comprehensive review on gender in teaching, rightly spell out that 'teaching is historically and culturally imbued with multiple discourses and subjectivities of gender' (p. 529). This chapter portrays gender identity construction, negotiation and renegotiation of two Hong Kong Chinese teachers, Shuijing and Baibin, who both have been involved in painstaking struggles with their gender identities but with varied learning backgrounds. Their narratives aim to illuminate understanding of: - How the gender identities of the Hong Kong Chinese male and female teachers were negotiated and renegotiated, their varied institutional experiences, and; - Crucial elements contributing to gender identity negotiations.