Expansion of Macedonia under Philip II in the context of "Philip II of Macedon"

Classical Greece was a period of around 200 years (the 5th and 4th centuries BC) in Ancient Greece, marked by much of the eastern Aegean and northern regions of Greek culture (such as Ionia and Macedonia) gaining increased autonomy from the Persian Empire; the peak flourishing of democratic Athens; the First and Second Peloponnesian Wars; the Spartan and then Theban hegemonies; and the expansion of Macedonia under Philip II. Much of the early defining mathematics, science, artistic thought (architecture, sculpture), theatre, literature, philosophy, and politics of Western civilization derives from this period of Greek history, which had a powerful influence on the later Roman Empire. Part of the broader era of classical antiquity, the classical Greek era ended after Philip II's unification of most of the Greek world against the common enemy of the Persian Empire, which was conquered within 13 years during the wars of Alexander the Great, Philip's son.

In the context of the art, architecture, and culture of ancient Greece, the Classical period corresponds to most of the 5th and 4th centuries BC (the most common dates being the fall of the last Athenian tyrant in 510 BC to the death of Alexander the Great in 323 BC). The Classical period in this sense follows the Greek Dark Ages and Archaic period and is in turn succeeded by the Hellenistic period.

Macedonia (/ˌmæsɪˈdoʊniə/ MASS-ih-DOH-nee-ə; Greek: Μακεδονία, romanized: Makedonía, pronounced [maceðoˈni.a] ) is a geographic and former administrative region of Greece, in the southern Balkans. Macedonia is the largest and second-most-populous geographic region in Greece, with a population of 2.36 million (as of 2020). Part of Northern Greece, it is highly mountainous, with major urban centres such as Thessaloniki and Kavala being concentrated on its southern coastline. Greek Macedonia encompasses entirely the southern part of the wider region of Macedonia, making up 51% of the total area of that region. Additionally, it widely constitutes Greece's borders with three countries: Albania to the northwest, North Macedonia to the north, and Bulgaria to the northeast.

Greek Macedonia incorporates most of the territories of Macedon, a Greek kingdom ruled by the Argeads, whose most celebrated members were Alexander the Great and his father Philip II. Before the expansion of Macedonia under Philip in the 4th century BC, the kingdom of the Macedonians covered an area corresponding roughly to the administrative regions of Western and Central Macedonia in modern Greece. The name Macedonia was later applied to a number of widely-differing administrative areas in the Roman and Byzantine empires. With the gradual conquest of south-eastern Europe by the Ottomans in the late 14th century, the name of Macedonia disappeared as an administrative designation for several centuries and was rarely displayed on maps. With the rise of nationalism in the Ottoman Empire, the name Macedonia was revived in the nineteenth century as a geographical term, and for educated Greeks it corresponded to the ancient historical land. The economic ascent of Thessaloniki and of the other urban centres of Macedonia coincided with the cultural and political renaissance of the Greeks. The leader and coordinator of the Greek Revolution in Macedonia was Emmanouel Pappas, today considered a Greek hero along with the unnamed Macedonians that fought with him.

Bardylis or Bardyllis (/bɑːrˈdɪlɪs/; Ancient Greek: Βάρδυλις; c. 448–358 BC) was an Illyrian king, and the founder of the first attested Illyrian dynasty. During his reign, Bardylis aimed to make Illyria a regional power interfering with Macedon. He united many southern Illyrian tribes under his realm and defeated the Macedonians and Molossians several times, expanding his dominion over upper Macedonia, including Lynkestis, and ruling over Macedon through a puppet king. Before the rise of Macedon, Illyrians were the dominant power in the region. Bardylis also led raids against Epirus, but his soldiers were eventually expelled from the region.

Most scholars hold that the Illyrian kingdom that was established by Bardylis was centered along Lake Ohrid and east to the Prespa Lakes, which was called Dassaretis later in Roman times, located on the border between Macedon and Epirus. Illyrians, in particular under Bardylis' leadership, held a remarkable role in the development of the Argead Macedonian military. Philip II and Alexander the Great spent at least some of their youth age at Illyrian courts, getting well familiar with Illyrian customs, habits and specially military strategies and techniques.

Pleuratus I (Ancient Greek: Πλευρᾶτος; ruled 356–335 BC) was an Illyrian king of the Illyrian tribe of the Taulantii. Pleuratus was the father of Glaucias. Pleuratus managed to defeat Philip II during Macedon's expansion, wounding the Macedonian king in the right leg.