Women entrepreneurs’ role is considered crucial for the overall economic development and growth. Entrepreneurship is embedded in the cultural norms and values of the society, and it affects the way individual define their behavior, activities in terms of risk taking proactiveness, the aim of this study is to investigate the influence of the two cultural dimensions of Hofstede’s model i.e., Masculinity and Individualism on the business performance of women entrepreneurs with special reference to small and medium enterprises. The Masculinity side of this dimension represents a preference in society for achievement while individualism indicates greater importance on attaining personal goals. The study intends to analyze the relationship of women entrepreneurship with cultural dimensions individualism and Masculinity in Pakistan’s two culturally diversified regions, Gilgit-Baltistan and Islamabad, home to large numbers of women entrepreneurs. To capture the diversity of these regions by using the technique of purposive sampling, a sample of 374 was collected, 51% participants from the capital city and 49 % belonged to GB. The findings indicate that regional cultures within the context of Masculinity and Individualism have significant but antagonistic influences on the business performance of women entrepreneurs.