This paper evaluates the competitiveness of the European Union (EU) and Russia's regime preferences in their foreign policies towards Ukraine in the scope of the ongoing Ukraine crisis. It is argued that the underpinning geopolitical environment Ukraine currently resides in, wedged between two much larger powers (the EU and Russia), renders it a vulnerable target state for regime promotion from both sides. Indeed, since the 2004 Orange revolution in Ukraine, both the EU and Russia have had discernible regime promotion strategies in their foreign policies. The EU's regime promotion has focussed on facilitating democracy in Ukraine, along with more material interests (trade and strategic aims) while Russia has reacted with increasingly zero-sum policies which pursue its preference for having a loyal and Russian-facing regime in Ukraine. Ultimately, the increasing competitiveness of the EU and Russia has been a key factor in the onset of the Ukraine crisis, which offers important insight into the relationship between large powers and the smaller third states which lie in their overlapping spheres of influence.