Timeline: Macedonian History at a Glance - Chronology of Key Events
-- CULTURAL REVIVAL -- - Part 02
August 1018, Basil II succeeded in destroying the last remnants of Samoil's forty-two year reign (976-1018) of his Macedonian kingdom. By now Basil II was an old man and after finishing with Samoil, he took his campaign to Armenia. Some historians believe
this was a mistake. By destroying Armenia he destroyed an effective buffer zone between the Pravoslavs (Byzantines) and the Islamic powers. Basil II died in 1025.
1040 - Petar Delian organizes a rebellion
Petar Delian organizes a rebellion (1040-1041) against Eastern Roman rule.
Besides regular taxes, Macedonians were also obliged to pay various supplementary taxes, like judicial fines, toll tax for crossing rivers, fishing tax, water-mill tax and marriage tax. As a marriage tax the groom was obliged to pay his bishop a gold piece and the bride twelve ells (15 meters) of linen.
By 1040, discontent with Pravoslav (Byzantine) rule, the situation in Macedonia reached a boiling point and the population began to rebel. Leading the rebellion was Peter Delian, Gabriel Radomir’s son by his first wife, the daughter of the Hungarian king. The rebellion, supported by the Hungarian king, began in the regions of Belgrade and Morava near the Hungarian border and soon spread south to Skopje. With popular support and assistance from the local Macedonian population, the rebel army invaded and took Skopje. Tsari Grad (Constantinople) quickly reacted by dispatching an army in pursuit. But instead of attacking, the Pravoslav soldiers defected and proclaimed Tihomir, one of their own soldiers, as their emperor. Tihomir unfortunately died in battle leaving his army under Delian’s command.
1072 - Giorgi Voiteh organizes rebellion
In 1072, five years after the Thessalian rebellion, a new revolt broke out, this time inside Macedonia. The revolt, led by George Voiteh, took place in Skopje and was sparked by new and more oppressive financial policies introduced by the Pravoslav (Byzantine) authorities. The leaders of the revolt turned for help to Michael, the ruler of Zeta, who was related to Samuel. Michael sent his son Constantine Bodin along with three hundred of his elite troops. Voiteh and his rebels met Bodin at Prizren and immediately
proclaimed him emperor under the name Peter, in honour of the fallen Peter Delian.
1185 - Macedonian feudal lord Dobromir Hrs becomes independent of Eastern Roman rule.
After Andronicus I Comnenus died in 1185, Isaac II Angelus replaced him as emperor. It was during Isaac II’s reign that the newly developed feudal powers in Serbia and Bulgaria were established and became a significant political factor in the Balkans. The sacking of Solun by the Normans weakened the Pravoslavs (Byzantines) and that too created favourable conditions for the Slavonic feudal lords to gain some independence. Among the more successful of these was Dobromir Hrs. Hrs had accumulated an army of five hundred men and, for the most part, maintained peaceful relations with the court in Tsari Grad (Constantinople). He was, however, an opportunist and looked for ways to expand his authority. His chance came in 1189 during the third Crusade, led by Frederic I Barbarossa, when a number of Crusaders left the main route and invaded Macedonia. While passing through Gradets they killed people and set fire to several buildings, including the town’s church. After descending to Vkahija (near Strumitsa) they clashed with a rebel group and took their possessions. It was here that Hrs made contact with the Crusaders and sent them on their way. Unfortunately no sooner had the Crusaders departed for Asia Minor than Pravoslavs rounded up these opportunistic feudal lords and sent them to jail. Dobromir Hrs was imprisoned for a while but was then released and awarded the governorship of Strumitsa.
1207 - Macedonian feudal lord Strez (1207-1214) becomes ruler of parts of Macedonia from Solun region to Ohrid.
After the 1205 defeat of the Latin Emperor Baldwin and the Adrianople Crusaders, the Bulgarian army attacked and destroyed the town Serres and invaded the district of Solun. Bulgarian pressure on Solun increased in 1207, particularly after the death of Boniface of Montferrat. The Bulgarian emperor Kaloian laid siege to the city but soon died and the siege was abandoned.
In the period after Kaloian's death a power struggle ensued in Bulgaria and Strez, a descendant of the Bulgarian royal line was able to establish an independent kingdom in Macedonia. With the aid of Serbia he set himself up in Prosek and extended his rule from Solun Region to Ohrid. All Bulgarian governors within these territories swore loyalty to him. After a while, agitation from the Bulgarians subsided and Strez was able to establish good relations with the Bulgarian state.
Upon consolidating his rule in Macedonia, Strez began a campaign against the Kingdom of Solun which in 1212 sparked a massive conflict in Pelagonia. Even though the conflict was between Strez and the Latins, it had support from the more powerful Despot of Epirus on one side and the Bulgarian state on the other. After losing to the Latins, Strez broke off relations with the Serbians. In 1214 he initiated a campaign against them but died unexpectedly.
After Strez’s death the Despot of Epirus conquered a large portion of Macedonia, including Skopje and Ohrid. In 1244 Solun too fell prey to the army of Epirus.
1255 - The Dragota Uprising
Another less known uprising termed the Dragota uprising named after its leader, took place in 1255 in the Melnik Region during Nicaean rule. In 1246, the Nicaean ruler John III Vatatzes conquered Melnik and the surrounding region and established Nicaean rule. The City Melnik and its vicinity being in mid-course of the Struma River always played a geopolitical role in Macedonia’s history. Important roads passed through there and connected the coast of the Aegean Sea with the Danube including Salonica with Sofia. On the road from Melnik to Seres, near Melnik, is the Rupel Gorge, a very important strategic position which allowed rulers of the city to control the main roads from north to south and from east to west. As a result Melnik developed through the centuries as a strong fortress, and has served as capital city many times through history reaching its zenith in the 13th century when it became Alexeus Slav’s capital.
Dragota was originally from Melnik but because of his military achievements in the Bulgarian army, he was appointed military
commander of Seres. After Emperor Ka1iman’s death in 1246 the Nicaeans invaded Macedonia. Dragota unable to resist their attacks allowed the region to fall in 1246. Afterwards he surrendered Seres to the Emperor John Vatatzes, and some time later helped the Nicaeans conquer the city of Melnik. He was greatly awarded for his help, and as a Nicaean Vassal was formally appointed commander of Melnik and the surrounding region.
1282 - Urosh II invades Macedonia
Then in 1282 the Serbian feudal army of king Stephen Urosh II Milutin invaded northern Macedonia and took Lower and Upper Polog, Skopje, Ovche Pole, Zletovo and Piyanets. Shortly afterwards, the Serbs initiated a new campaign and invaded Poreche and the Kichevo and Debar regions. After that a Serbian detachment was dispatched along the lower course of the Struma River and penetrated as far as Krstopol.
About four decades later the Serbians, under the rule of the Serbian King Stephen Urosh III Dechanski, launched another campaign against the Byzantines. During their first wave of attacks they invaded and captured the towns of Shtip, Chreshche on the River Bragalnitsa, Veles and Prosek on the Vardar. Then in 1328 they took Prosek and the Serbian army invaded the regions of Demir Hisar and Debartsa, coming face to face with the Byzantines in Ohrid.
Ohrid was an important Byzantine stronghold and the threat did not go unnoticed in Constantinople. Emperor Andronicus III Palaeologus immediately prepared a counter-offensive and went in pursuit of the invaders. By 1330 the Emperor had recaptured the towns in the Demir Hisar and Debartsa regions, including Zheleznets.
Four years later, under the leadership of their new ruler Stephen Urosh IV Dushan, the Serbs renewed their offensive in Macedonia. With the capture of Serres in 1345, Serbian rule was extended over virtually all of Macedonia. The same year the Serbian ruler Stephen Urosh IV Dushan proclaimed himself emperor and elevated the Serbian Archbishopric to a Patriarchate. The coronation took place
in Skopje on April 16, 1346 but the Byzantines refused to recognize it along with Serbia's territorial gains and the Serbian Patriarchate.
During the course of the late 1340’s Serbian rule was expanded to Thessaly and Epirus. But in 1350 the towns of Serres and Voden rebelled and severed links with the Serbs. After that opposition became common everywhere and the Serbs found it very difficult to hang on to their conquered territories.
After Stephen Urosh IV Dushan’s death in 1355 the central government's authority quickly eroded, leaving the feudal lords to rule independently. The most notable of the feudal lords in Macedonia at the time were the brothers Volkashin and Uglesha. Volkashin proclaimed himself king in 1365 with Emperor Urosh as co-ruler.
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Printed from https://macedonianhistory.ca/narrative/chronology/9 on October 29, 2026