The relevance of the article is that the nineteenth century was a time of profound transformations of legal systems. The Romano-Germanic and Anglo-Saxon types of law were clearly distinguished. From the second half of the XIX century. on the European continent are beginning to form modern states for which were dominated by three main forms of statehood: empire, federation and confederation. The republican form, which was just being established, did not become widespread due to the colonial orientation of the world at that time. A republic based on the principles of democracy could not, in essence, be a metropolis and own colonies. The purpose of the article is a historical and legal analysis of the dynamics of the "Ukrainian question" in the second half of the nineteenth century. The article examines the historical and legal features of the evolution of the "Ukrainian question" in the second half of the nineteenth century. It is established that at the turn of the XIX-XX centuries. The "Ukrainian question" became widespread within the framework of international legal doctrines. It is determined that the "Ukrainian question" aroused special interest in the conditions of relations between the Russian, Austro-Hungarian and German empires. It is emphasized that the essence of the "Ukrainian question" of the second half of the XIX century was that in the international arena it posed a greater threat to the Russian Empire than in the domestic one. The reason for this was that the Ukrainian national liberation movement focused on the ideas of autonomy and possible reform of Austria-Hungary and Russia on the basis of the federation. On the other hand, German pressure, which was associated with the declaration of the idea of the revival of a separate Ukrainian state, was aimed not so much at achieving a military conflict with Russia as at subordinating its political interests. It is concluded that at the turn of the XIX-XX centuries. The "Ukrainian question" became widespread within the framework of international legal doctrines. It aroused special interest in the relations between the Russian, Austro-Hungarian and German empires. First, each of these countries made expansionary plans for Ukrainian territories. Secondly, German and Austrian politicians actively developed the idea of reviving a separate statehood in the Ukrainian lands, which was to provide Ukrainians with the historical right to their own state.