Following Russia’s annexation of Crimea in 2014, or according to Russia, its accession following a referendum, Ukraine brought several international cases against the Russian Federation, including two cases under Annex VII of UNCLOS: The Dispute Concerning Coastal State Rights in the Black Sea, Sea of Azov, and Kerch Strait in 2016 and The Detention of Three Ukrainian Naval Vessels in 2019. At the center of these disputes is the conflict between Ukraine and Russia over sovereignty of Crimea. Russia contested jurisdiction in all cases invoking different exceptions under UNCLOS, including the argument that the dispute concerns sovereignty over Crimea and thus does not concern the interpretation or application of UNCLOS. In the Coastal State Rights in the Black Sea, Sea of Azov, and Kerch Strait, although the Annex VII Tribunal upheld Russia’s objection that the core issue underlying Ukraine’s claims was sovereignty over Crimea and thus precluded under UNCLOS Article 288(1), it proceeded to reject Russia’s objections to jurisdiction on other grounds. Similarly, in its order on Ukraine’s request for provisional measures, ITLOS granted provisional orders and concluded that the Annex VII arbitral tribunal would have prima facie jurisdiction. The article examines these cases in light of the historical context of the conflict over Crimea and the Black Sea fleet from the period of the Ottoman Empire, the USSR and the period following the dissolution of the former USSR. These cases present an important addition to the recent trend of cases where the underlying disputed sovereignty matters are brought under the UNCLOS dispute resolution procedures.