Over the recent decades the problem of Faroese and Greenland’s secessionism has become immensely pressing both for Denmark and the whole world, particularly in the face of growing geopolitical and military political instability. The authors intend to assess the probability of the dissolution of the Danish Commonwealth of the Realm and, as a consequence, to anticipate eventual international political scenarios. Firstly, the current legal statuses of the autonomous territories and their historical evolution were analyzed. Secondly, the phenomenon of metropolis’ transfers as an instrument of neocolonial policy was studied, demonstrating the relationship between the level of dependence of a self-governing territory on economic aid from the core and the desire and/or willingness to pursue independence. Thirdly, the economic and politico-military factors determining the rise of separatism in the islands were investigated. Despite the steps taken by Copenhagen to contain secession, the situation is developing in an evolutionary way, which allows authors to make a prediction about the modification of the Danish Commonwealth of the Realm into a «free association».