Following the so-called ‘44-Day War’ in late 2020, Azerbaijan and Armenia lodged reciprocal legal actions before the International Court of Justice and the European Court of Human Rights, alleging various breaches of international law. These inter-state claims encompass three decades and several claims under the UN Convention on the Elimination of All Forms of Racial Discrimination and the European Convention on Human Rights. Consequently, the judicialization of the conflict has added a new dimension in Azerbaijan– Armenia relations that was absent in the past 30 years of peace negotiations. This article analyses the ongoing inter-state legal cases and their legal and political consequences for the parties and the South Caucasus region at large. The article argues that these international legal forums can partially answer some of the transitional justice issues, but not all matters arising from this three-decades-long conflict. Despite such limitations, however, these international legal cases will likely bring more legal accountability and a ‘rule-based order’ between Azerbaijan and Armenia, and in the South Caucasus region, in the future.