In the context of the crisis in Ukraine and over Ukraine that has brought the Russia-West relations to a breaking point for the first time since the end of the East-West confrontation, it comes as no surprise that people are now asking themselves if we are heading towards a new Cold War. The Ukrainian crisis is viewed as the first direct conflict between differing regional strategies of Russia and the EU – Brussels’ Eastern partnership and Moscow’s Eurasia Union concept. Ukraine has been central to both strategies, and “the either/or” choice presented to Kiev ultimately made a conflict inevitable. However, the reason for this confrontation goes much deeper than the clash of two opposing regional strategies and is rooted heavily in the 1990s. Therefore, the Ukrainian conflict should be viewed as the quintessence of the mutual disappointment of Russia and the West, resulted from their mistakes after the end of bipolarity.