This article analyzes firm entrepreneurial orientation across different contexts. In the light of the existing literature on entrepreneurship and institutional theory, it departs from the hypothesis that the context in which firms operate determines the importance of each dimension comprised in the multidimensional concept of entrepreneurship orientation, thus moderating its effect of on firm performance. The sample for this study is composed of both small and medium-sized firms from three countries: China, Mexico, and Spain. In the means of testing our hypothesis and thus quantifying the moderating effect of context, a structural equation model PLS-SEM technique and, specifically, a multigroup analysis approach has been implemented. The results have led us to confirm an overall positive effect of entrepreneurial orientation on firm performance regardless of firm context. However, the context of a firm certainly acts as a moderator by determining the effect of entrepreneurial orientation on firm performance. This effect is explained by the conditioning power of context over innovation, proactiveness, and risk-taking, the three main factors defining firm entrepreneurial orientation across contexts.