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This chapter examines experts’ perceptions of the conditions of their entrepreneurial ecosystems to analyse women’s disadvantages, identify which conditions can improve in comparison to men in Latin America, and if the level of development of their country affects the support women entrepreneurs have. The study is based on regional data collected in Chile and Mexico with one of the Global Entrepreneurship Monitor surveys between 2015 and 2018. With a total sample of N = 2,230 male and female experts, the author uses principal component analysis and non-parametric statistics to compare means between genders and also women in different countries. First, male and female experts’ perceptions are compared at the macrolevel and then total women as a subsample are compared between the women experts’ perceptions by country at the mesolevel. At the macrolevel, the results show a clear perceived disadvantage for women entrepreneurs in all conditions except internal market dynamics. At the mesolevel, the findings show that support for women entrepreneurs is better in most conditions for Mexico, which is a less developed country, in comparison to Chile for this case. This chapter goes from studying the general to the particular issues causing gender gaps in entrepreneurial ecosystems in developing Latin American countries. The dataset used represents the biggest data-gathering project in the field of entrepreneurship for the region.