- Paeonia kingdom (Pre-Roman era)
- Achaemenid Empire (550 - 330 BC)
- Greco-Persian Wars (499 - 449 BC)
- Dardania kingdom (393 - 28 BC)
- Macdonia (808-168 BC, 150-148 BC)
- Upper Macedonia is annexed to Macedonia (336 BC)
- Byzantine Empire (395 - 1453 AD)
- First Bulgarian Empire (681 - 1018 AD)
- Ottoman Empire (1299-1922)
- Bulgaria kingdom (1908-1946)
- Balkan Wars (1912-1913)
- World War I (1914-1918)
- South Serbia (1919-1922)
- World War II (1939-1945)
- Greek Civil War (1943-1944)
- Yugoslavia Socialist Republic of Macedonia (1944-1991)
- Macedonia gains independence (1991)
- Macedonian insurgency (2001)
- Macdonia renamed to North Macedonia (2018)
(This post includes any nation or civilization that occupied at least a portion of North Macedonia at some point. Unless specified otherwise, the dates correspond to when a nation or civilization existed, but do not necessarily correspond to occupation of North Macedonia.)
