The Battle of Velbuzhd took place on July 28, 1330, in the vicinity of Velbuzhd (present-day Kyustendil), between the Bulgarian army led by Tsar Michael III Shishman Asen and the Serbian army led by King Stefan Uroš III Dečanski. It ended in defeat for the Bulgarians.
The Serbian kingdom, taking advantage of the internal strife in Bulgaria and Byzantium, as well as the constant clashes between them, managed to conquer part of their territories. Michael III Shishman began preparations for the conquest of Serbia, whose ruler was Michael's former brother-in-law Stefan Dečanski. For some historians, Mikhail Shishman is the only Bulgarian king (after the death of Ivan Asen II) who tried to stop the “Serbian expansion“ and to return to Bulgaria its western territories, even though they had been conquered by Byzantium. To this end, in the spring of 1330, he concluded an anti-Serbian alliance with the Byzantine emperor Andronicus III Palaeologus. According to most assumptions, the ultimate goal was the complete destruction of the Serbian Kingdom and the division of its lands between Bulgaria and Byzantium. Mikhail Shishman attracted the rulers of Wallachia, Moldavia and the Black Jassy to the coalition.
On June 19, 1330, the Bulgarian troops set off from Tarnovo, but instead of heading straight for the Serbian border, they passed through Vidin and Sofia. The reason for this unusual detour is usually given as the desire of Mihail Shishman to unite his army with that of his brother Belaur, but since his brother arrived after the end of the battle, it is clear that the Tatar mercenaries of Kara Kisek, son of Chaka, had joined Vidin. The Wallachian voivode Ivanko I Basarab, who was the father-in-law of the Lovech despot Ivan Alexander and an ally of the Bulgarian king, also joined Shishman's army.
Andronikos III entered Macedonia, capturing four small fortresses (Debritsa, Dobrun, Gabalarion and Siderokastron) and settled in a camp near Bitola, awaiting further developments. From Sofia, the Bulgarian army headed for the fortress of Zemen and captured it. Stefan Dečanski initially waited for his former father-in-law on the Dobrich field at the confluence of the Toplica River with the Bulgarian Morava River, and subsequently sent his army along the Morava River and through Staro Nagoricane, where he prayed for peace in the church of "St. George", and set up camp in the vicinity of Velbažd. Most researchers assume that the troops of the two rulers were approximately equal in number. According to Nikifor Grigora, Mikhail Shishman had 12,000 Bulgarians and 3,000 "Scythians" (Tatars, Yassians, Alans and Vlachs). Stefan Dečanski had 14,000 men at his disposal, who were later joined by 300 (according to Kantakouzenos) or 1,000 (according to Grigora) Catalans from the famous Catalan Company (Spanish mercenaries from the Catalonia region). It was precisely while waiting for them that on July 24, Stefan Dečanski offered Mikhail Shishman a one-day truce. The tsar accepted because the army lacked provisions. It was established that Belaur did not join his brother, nor did Ivan Alexander. Since the Bulgarian army suffered from a lack of food, on the day of the truce, it scattered to the surrounding villages to procure it.
Taking advantage of the advantageous situation, the Serbian Crown Prince Stefan Dušan violated the truce and attacked the Bulgarian camp. Mikhail Shishman's attempt to organize effective resistance was unsuccessful. Mikhail Shishman's army suffered a defeat, and the tsar himself was seriously wounded and died three days later in captivity. He was buried at the request of his nobles in the church of "St. George" in Staro Nagoricane, today in North Macedonia. Michael III Shishman was the last Bulgarian ruler to pursue a policy of establishing military and political hegemony of the Kingdom of Tarnovo on the Balkan Peninsula.