Skopje (Macedonian: Скопје, [ˈskɔpjɛ] ( listen)) is the capital and largest city of the Republic of Macedonia with about a third of the total population. It is the country's political, cultural, economic, and academic centre. It was known in the Roman period under the name Scupi.

The territory of Skopje has been inhabited since at least 4000 BC; remains of Neolithic settlements have been found within the old Kale Fortress that overlooks the modern city centre. On the eve of the 1st century AD, the settlement was seized by the Romans and became a military camp. When the Roman Empire was divided into eastern and western halves in 395 AD, Scupi came under Byzantine rule from Constantinople. During much of the early medieval period, the town was contested between the Byzantines and the Bulgarian Empire, whose capital it was between 972 and 992. From 1282 the town was part of the Serbian realm and its capital city since 1346. In 1392 the city was conquered by the Ottoman Turks who called the town Üsküp. The town stayed under Ottoman control over 500 years, serving as the capital of pashasanjak of Üsküb and later the Vilayet of Kosovo. At that time the city was famous for its oriental architecture. In 1912 the city was conquered by the Kingdom of Serbia during the Balkan Wars and after the First World War the city became part of the newly formed Kingdom of Serbs, Croats and Slovenes (Kingdom of Yugoslavia). In the Second World War the city was conquered by the Bulgarian Army, which was part of Axis powers. In 1944 it became the capital city of Democratic Macedonia (later Socialist Republic of Macedonia), which was a federal state, part of Democratic Federal Yugoslavia (later Socialist Federal Republic of Yugoslavia). The city developed rapidly after World War II, but this trend was interrupted in 1963 when it was hit by a disastrous earthquake. In 1991 it became the capital city of independent Macedonia.