Since its independence in 1991 Estonia has successfully overpassed the challenges of the transition period being in the present of one the most technologically developed nations of Europe. The present research is intended to evaluate the relationship between Estonian pro-market regulation, entrepreneurship and innovation. In order to reach relevant conclusions in this regard there have been used both qualitative and quantitative methods of analysis. In such a way, it could be comprehensively reviewed the process of Estonian economic development from a relatively underdeveloped USSR republic to an advanced innovation driven economy. The results show that pro-market governmental regulation has favourably influenced Estonian entrepreneurship, while it fostered country’s innovation capacities. It has been concluded that the economic “miracle” of Estonia has been at a great extent determined by proper government regulation oriented towards economic liberalisation.