The dissolution of the USSR at the end of December 1991 and the reunification of Germany were, without doubt, two of the most remarkable international events at the end of the 20th century. Analysis of the consequences of these events with respect to international law has proved challenging to international legal norms due to the fact that the kind of “micro cosmos” exemplified by these events served to highlight the principal sectors of international law. The consequences of the dismemberment of the USSR proved to be extensive and they were felt not only in Europe, but also in the rest of the world. The breakup of such a prominent strategic actor put an end to the restricted stability that characterized the bipolar nature of the Cold War. Thus, international society witnessed a period of instability in succeeding years marked by a renewed rise in issues such as the right of self-determination and the principle of uti possidetis. Therefore, events unfolding in the former Soviet Union, at times tedious and even tragic, led to the creation of a new international organization called the Commonwealth of Independent States, which tried to fill the “black hole” left by the breakup of the USSR as well as deal with the problems confronted by the successor states, notwithstanding its own deficiencies. Moreover, some disputes of a territorial, interethnic, or national character became very violent, such as those in Central Asia and the Caucasus, in particular in Georgia. Over the years Georgia has intensified its process of approximation to the European Union (EU). On the one hand, the EU-Georgia Association Agreement that entered into force on 1 July 2016 is remarkable for establishing a deep and comprehensive free trade area. On the other hand, the effective application of the Schengen—visa-free travel for short stays for Georgian citizens—has been of great importance. This article provides researchers with instruments to study the recurring problems in South Ossetia and Abkhazia, as well as the Georgian-Russian conflict in 2008, and also treats the consequences of these crises in international law. Issues such as military operations, the cease-fire agreement, and the succeeding evolution of events are discussed. A section focuses specifically on important violations of international law that took place during the conflict, for which an international report was published. In addition, the consequences of the conflict are addressed with respect to NATO-Russia and EU-Russia relations while the effects of the conflict in the geostrategic and energy fields are also considered. Additionally, the rapprochement between Georgia and the European Union is analyzed.