An explanatory survey was carried out in 2008 to investigate the relationship between Entrepreneurial Orientation (EO), environmental factors, human capital and organizational characteristics vs. entrepreneurial performance among entrepreneurial firms in Iranian agricultural sector. Data were obtained from a sample of 120 Iranian agricultural establishments, using an interview-oriented questionnaire. The hierarchical regression analysis revealed that: although there is a positive direct relationship between EO and entrepreneurial performance in an agricultural business setting, applying main effect or contingency models only, provides a distracting picture of entrepreneurial performance in agricultural settings. It was also found that configurational approach may better explain the relationship between EO, environmental factors, human capital and organizational characteristics vs. entrepreneurial performance over and above contingency and above main- effect models.