[3][4][5][6][7][8] Archaeologists have discovered fine pottery[9] and objects of everyday life on Nebet Tepe from as early as the Chalcolithic, showing that at the end of the 4th millennium BC, there already was an established settlement there.

Ten years after the Macedonian invasion the Odrysian king Seuthes III revolted against Alexander the Great's rule resulting in neither victory, nor defeat, but stalemate.

In 72 BC the city was seized by the Roman general Marcus Lucullus[21] during the Third Mithridatic War but was soon restored to Thracian control.

[26][27] Roman times were a period of growth and cultural excellence[28] and the ancient ruins tell a story of a vibrant, growing city with numerous public buildings, shrines, baths, theatres and a stadium.

The large scale of public construction during the Flavian Dynasty (69-96 AD) led to the city being named Flavia Philippopolis.

[32] Philippopolis fell to the Bulgars of the First Bulgarian Empire in 863, during the reign of Boris I (r. 852–889), having been briefly abandoned by the Christian inhabitants in 813 during a dispute with the khan Krum (r. c. 803 – 814).

[33][34] During the Byzantine–Bulgarian wars, the emperor Basil the Bulgar-Slayer (r. 960–1025) used Philippopolis as a major strategic fortification, governed by the protospatharios Nikephoros Xiphias.

The city continued to prosper, with the walls restored in the 12th century, during which the historian and politician Niketas Choniates was its governor and the physician Michael Italikos was its metropolitan bishop.

According to the Latin historian of the Fourth Crusade, Geoffrey of Villehardouin, Philippopolis was the third largest city in the Byzantine Empire, after Constantinople (Istanbul) and Thessalonica (Thessaloniki).

The initial planning and construction of Philippopolis started during Philip II's rule (359–336 BC) and continued during the reign of Alexander the Great and the Diadochi.

The first city wall of Philippopolis was built as early as the 4th century BC and fragments of this fortification system are visible today on the northern and northwest slopes of Nebet Tepe.

The wall was provided with small gates that led to passages or tunnels inside the rock through which steps reached the northern foot of the hill.

[36] In the 2nd c. AD, the area north of the forum was enhanced and important public buildings from the Hellenistic period like the theatre, the stadium, the agora, treasury and odeon were rebuilt and expanded.

Three aqueducts of 22 km length supplied mainly the lower part of the city, while the hills relied on wells and rainwater tanks.

The aqueducts run in parallel in the neighbourhood of the suburb of Komatevo at a separation of 30-40m, one a pipeline of clay pipes and two carried partially overhead on arches.

[40] It is assumed that the three aqueducts converged on the western slopes of Djendemtepe into a distribution tank (castellum aquae) which seems to have been destroyed in the construction of the modern tunnel.

The catchments at Markovo are well researched; one of them is an underground reservoir measuring 13 × 7 m, partially destroyed; the second is a complex tunnel system: a central gallery and side branches.

Notable buildings that can be seen today are the: The enormous Great Basilica with its magnificent floor mosaics has been excavated over many years and is now preserved in a new museum (2021).

[42] In 2018, a fragment from a Roman statue with an ancient Greek inscription was found which mentions the right of “proedria" (the right to take front row seats in the theatre.

The inscription reads: “For the victory, the health and the eternal existence of the emperors, Publius, Licinius Valerian and Gallien Augustin and for their whole house, for the holy senate and Roman people, and for the council and people's assembly of Philippopolis – the Thracian leader Dionysus dedicated the surviving mysteries, while the leader of the mysteries and eternal priest was Aurelius Mukianid, son of Mukian”.

In act III of scene 1, Major Sergius Saranoff and Paul Petkoff assist the help of Captain Bluntschli, to help them move three regiments of cavalry to Phillippopolis despite a shortage of forage.