During the past 500 years, Iran and Russia have experienced many ups and downs in their relations which have been accompanied with enmity and amity. These relations varied from cooperation under the Safavids to enmity, war and interventions under the Qajar dynasty, then to hostile and sometimes friendly relations under the Pahlavi rule, and finally to collaborations within the past two decades (1989-2009). This paper seeks to analyze the 20-year collaborations between the two countries in various fields and study domestic, regional and world grounds affecting the formation of such ties. Then it examines the new geopolitical situation (Russia's distancing from Iranian borders) as a crucial variable. Indeed, the paper is mainly intended to address the impact of geopolitical developments on the bilateral cooperation during the past 20 years, avoiding the problems which have occurred within the one past year.