This chapter explores gender differences in Nigerian men and women’s leadership practices and collective entrepreneurial behaviour. The rationale stems from the fact that very little is known about leadership and collective entrepreneurial behaviour of Nigerian entrepreneurs; as such, the chapter adds to the literature on leadership and entrepreneurship in the Nigerian context. The review for the study is drawn from a combination of the entrepreneurship and leadership literature, with particular reference to transactional, transformational leadership styles and collective entrepreneurship. Data for the study were obtained from a face-to-face questionnaire survey with 360 male and female entrepreneurs in Lagos, Nigeria. The findings show remarkable differences and unique similarities in the leadership and entrepreneurial behaviour adopted by men and women. The study has several theoretical implications. It helps fill to gaps in the literature on leadership and entrepreneurship in Nigeria, thereby providing a theoretical perspective on which future research can be developed.