[5] The Roman settlement of Turres (Latin for "towers"), which was a military residence, is mentioned in the first half of the 3rd century.

In times when the Slavs and Avars were invading the Balkans, the settlement was named Quimedava, and was situated on the southern slope of the Sarlah Hill.

Corresponding to the archaeological investigations, the town back then, surrounded by forts and fortified walls, also included an early Christian basilica, thermae (public baths), a necropolis, and other facilities.

[7] In 1153, Arab geographer Burizi crossed the country, and recorded the place of Atrubi at the site of old Turres, describing it as situated by a small river which arrives from the Serbian mountains and was a tributary of the Morava.

[7][verification needed] In 1182–83 the Serbian army led by Grand Prince Stefan Nemanja conquered Byzantine territories from Niš to Sofia.

In 1331-1332 Church of St. Petka in Staničenje was built - at the time of Bulgarian Emperor Joan Asen (Ivan Alexander) and Vidin master Belaur.

1578) recorded that Pirot Christians claimed that the town was the earlier estate of Miloš Obilić, the slayer of Sultan Murad at Kosovo.

[20] In 1659, Austrian deputy August von Mayern visited the town and described it as "Schiarchici, a town called by the Orthodox as Pirot, but is not surrounded by walls and inhabited by Turks and Rascians" (Rasciani according to the author were even the citizens of Sofia, Ihtiman etc.).

[21] In 1664, Austrian deputy Leslie and English nobleman John Burberry visited the town, the latter noting that there were three churches, one of which was earlier Dominican.

[22] During the Great Turkish War, after taking Niš on 25 September 1689, Austrian general Piccolomini with his army of Serb volunteers and some Germans chased Turks towards Sofia.

[22] In August 1690 a large Ottoman army took Pirot, defended only by 100 Germans, and then besieged Niš, taking it after three weeks.

[23] Hungarian detachments retreating via Temska ravaged the monastery and terrorized the surrounding population, as inscribed by a priest on the church walls.

[23] The first known literary monument, influenced by Torlakian dialects is the Manuscript from Temska Monastery from 1762, in which its author, the Monk Kiril Zhivkovich from Pirot, considered his language as "simple Bulgarian".

[25] Ibrahim Pasha, unable to enter Serbia cross Aleksinac and Deligrad, planned to attack from Pirot and Lom with the intent to clash with the Serbian army before Niš; the Serbian army went to stop this and defeated him in the mountains between Pirot, Knjaževac and Chiprovtsi.

[26] Carpetry was the main occupation, there were many shops and cafés in the centre, the population was mixed, and it was the domain of the sister of the Sultan.

[29] In the 19th century Johann Georg von Hahn stated that the Christian population of Pirot is Bulgarian.

Philipp Kanitz claimed that some inhabitants "Did not imagine that six years later the cursed Turkish rule in their city would end, and even less, because they always felt that they are Bulgarians, that they would belong to the Principality of Serbia".

[38] During World War I, the Bulgarian army entered Pirot on 14 October 1915 and occupied the city as well as the whole Pomoravlje region.

[39] In the Interwar period, the Internal Western Outland Revolutionary Organization engaged in repeated attacks against the Yugoslav police and army.

During World War II Bulgaria occupied the so-called Western Outlands, as well as Pirot and Vranje.

On the territory of the city of Pirot operates tire manufacturer Tigar Tyres which is one of top Serbian exporters in the period from 2013 to 2017.

Асена : и при господине Бе(лауре)..Средином 70-тих година XIV века пиротски краj изгледа улази у оквир старих српских земља под влашћу кнеза Лазарапа затим закључуjе "да jе ово било значаjно место у Бугарскоj и да су овде живели кнезови"