Vinkovci is located in the northernmost meander of Bosut, whose left bank, positioned about 88 metres above sea-level, was protected from frequent floods and suitable for colonization. Owing to its favourable position, Vinkovci was an area upon which the cultures used to inherit one another from early Stone Age to modern times. Not the same sites were always inhabited, but looking at the current layout of the City, Vinkovci has been continually inhabited for over 8,000 years. Most of the prehistoric settlements were situated on that high left bank, and the largest and longest lasting settlement was formed on the right confluence of the Ervenica brook into Bosut, on "Telo Tržnica".
The first communities of farmers settled this area around the year 6200 B.C., introducing pottery, domesticated animals and plants.

Colonia Aurelia Cibalae was the third largest city in the province of Pannonia Secunda, which covered the area of the modern-day Slavonija, Syrmia and Baranya, after the capital of Syrmia (S. Mitrovica) and Mursa (Osijek). The City was founded at the beginning of the 1st century and slowly developed into a trading and craftsmen centre. It is not known what the City was originally called, however, during the reign of Hadrian (117-138) it received the status of a municipium (Municipium Aelium Cibalae), and at the end of the 2nd or the beginning of the 3rd century, the City was elevated to the rank of colony. The basis of commercial development were agriculture and the pottery industry, which is testified by more than 80 discovered pottery kilns so far. The City reached the pinnacle of its development in the 4th century, when between 5 and 10 thousand inhabitants lived in the City and its surroundings, and the City covered the surface area of about 550,000 m2. Apart from the fact that as early as the first half of the 2nd century there was a Christian diocese and that we are familiar with the names of one of the bishops (Eusebius (?-258)) and one of the scribes (Polion(?-304)), the most important people born in Cibalae were Valentinian (364-375) and Valens (364-378), brothers and the only Roman emperors born on the territory of the modern-day Republic of Croatia.
The transition from the Antiquity to the Middle Ages is noted by the mobile finds and the graves dating from the 5th century, and they are associated with the indigenous romanized population and barbarian federates.

At 14 Cibalae intra muros sites, 52 graves from the beginning of the Middle Ages were explored.

The settling of the Slav tribes resulted in the moving of the centre of the City towards west. At the 99 Duga Street site, ten burn graves were discovered.

Around the end of the 11th century, in the western outskirts of Cibalae, a new settlement was founded. The inhabitants of that settlement raised a small church in the Romanesque style, whose foundations were uncovered. That church was without a doubt dedicated to Sv. Ilija (St. Elias). With the same name, right next to the southern side of the small early-Romanesque church, a larger Gothic parish church was built, of which we can say with complete certainty that it bore the name of St. Elias. On several occasions, around these two churches, total of 329 graves were explored, most of which are from early Modern Period (17th-18th century). In the 19th century, the purpose of the Gothic church was changed to serve as a granary, and it represents the oldest self-standing building in the City of Vinkovci.

It would seem that the Middle Ages settlement had one other, older name, which was Bogdanfalva.

Vinkovci (Wynkocz), as one of the nearby "Sv. Ilija" satellite villages, was first mentioned in 1491. The area of the Middle Ages settlement of Sv. Ilija, or the modern-day Vinkovci, fell completely into Ottoman hands with the fall of Ivankovo in 1536. The larger Middle Age settlement of Sv. Ilija was most likely ravaged at that point, and so in the Ottoman tax record from around 1570, Vinkovci is mentioned, which was back then comprised of 17 houses and whose inhabitants, among other things, tended the farmlands of the Ilinci moor village = Sv. Ilija. This particular Vinkovci, according to a similar record from around 1630, was comprised of 16 houses. Throughout the entire Turkish period of the 16th and 17th century on the site of the modern-day Vinkovci, aside from Vinkovci, there were only 4 more inhabited villages: Zalužje (in 1570 - 21 houses), Trbušanci (in 1570 - 23 houses), Draganovci (in 1570 - 13 houses) and Liskovac (in 1570 - 8 houses). The area of the Ottoman Vinkovci (karye-i Vinkofçi) around the end of the 17th century, was devastated in the liberation war operations, and the population was forcibly displaced. During the Turkish disaster and the exile in the years 1690 and 1691, the citizens of Vinkovci were hiding at Antinske bare and other safer places, and the same was done by the the inhabitants of the surrounding villages. The return of those citizens to their old villages, as well as Vinkovci, commenced around 1700.

At the beginning of the 18th century, Vinkovci found itself in the territory of the newly-established (in 1702) Slavonian Military Frontier. According to the canon visitation from 1729, it is apparent that the old Gothic parish church at Meraja received the dedication to St. Vincent the Martyr, while in the Middle Ages it used to bear the dedication to St. Elias.

In 1750 Vinkovi became the headquarters of the 7th Brod Frontier Regiment (founded in 1747), and between 1765 and 1785, it had the status of a military community, which was an indication that a relatively large craftsmen population inhabited it. This was strongly reflected in the demographic and commercial development of Vinkovci, and so in 1789 it had about 2,000 souls, unlike the year 1738 when there were only about five hundred. So, Vinkovci, by the end of the 18th century, transformed from a large village into a smaller Military-Frontier townlet with dominant administrative, craftsman and trade functions, whose task was to satisfy the needs of both the military and the Frontier population which inhabited the territory of the then Brod Regiment.

In 1765, which was the year of the founding of the Military Community in Vinkovci, 67 Frontier families lived in Vinkovci, and 90 craftsman families, the latter absolutely outweighing the former. As an acknowledgment of their significance, this craftsman population received their "Vinkovci Guild Privilege" in 1774 from Empress Maria Theresa. This predominantly craftsman and trading significance of Vinkovci with the aforementioned central administrative and other functions, would remain a constant in the later periods as well, and we could say, all the way until the first half of the 20th century, when the dominance over the craftsmen would pass to the manufacture and the industrial plants such as steam mills and saw mills, brickworks, textile, tannery and other plants.

On the trail of the mentioned Vinkovci social conjuncture, in the second half od the 18th century a line of solidly built both public and private late-Baroque buildings was constructed or founded in Vinkovci. In 1762 the elementary school was founded; in 1777 the construction of a new great late-Baroque church of St. John Nepomuk (modern-day St. Eusebius and Polion) was completed; between 1780 and 1785 a great representative one-storey building of the 7th Brod Frontier Regiment Headquarters and Main Guard was being built (the modern-day Vinkovci City Museum); and since 1779/92 a grammar school has been operating in Vinkovci. In that same period, the central City square, at that time still known as the military "Paradeplatz" received its final architectonic and urbanistic shape which it still possesses even today (naturally, including the later redesigns and refits).

In 1857, Vinkovci (not counting Neudorf and Mirkovci), at the time of the first official census carried out in the Austrian Empire, had 628 houses in which 3113 citizens lived, of which 2489 were of the Roman-Catholic and 442 of the Orthodox, 180 of the Evangelist, 1 of the Greek-Catholic and 1 of the Calvinist religion.

At that time, more precisely around the year 1830, there were total of 11 taverns and inns in Vinkovci, and for modern standards rather colourful names:

  1. Winkowzer Militar Wirtshaus («Vinkovci Military Tavern» – it was the erar, or state property); 
  2. Beim schwarczen Rössel («Black Rose's»); 
  3. Beim Hirschen («Deer's»); 
  4. Beim grünen Baum («Green Tree's»); 
  5. Einkehr Wirtshaus und Bräuhaus («First Tavern and Alehouse»); 
  6. Beim weissen Wolfen («White Wolf's»): 
  7. Beim Posthorn («Post Horn's»); 
  8. Beim Ochsen («Bullock's»); 
  9. Bei der silbernen Kugel («Silver Ball's»); 
  10. Beim goldenen Fassel («Golden Jug's»); 
  11. Beim Shützen («Archer's»).

Of the notable institutions which appeared in Vinkovci at that time, are surely the Girls School, founded no later than in 1815, which at that time operated at the ground level of the "Generalije" Building (later the Brod Municipality Building) and Regiment Hospital since 1831 (at first in the building of the 7th Brod Regiment Command, then as of 1857 in the newly-constructed building in the modern-day Zvonimirova Street (today the Health Centre).

The demilitarization in 1873 and the incorporation of the Military Frontier into the rest of the Triune Kingdom in 1881 were the next turning point in the demographic and social development of Vinkovci. The crucial event for the development of Vinkovci in this period was the arrival of the railway in 1878 (from the direction of Dalj and Budapest, then toward Slavonski Brod), as well as the beginning of intense exploitation of oak forests.

In the period between 1880 and 1910, the three oldest Vinkovci ethnic communities suffered a certain loss in percentage: Croats, as much as 6,5%, Serbs 2,2%, Germans 1,5%, while the people who rose in number were the Hungarians, who increased their percentage by even a factor of three in thirty years, and Jews by 1,1%. That increase between 1880 and 1910 coincided with the pro-Hungarian regime of Viceroy Khuen-Hédérváry (Croatian viceroy from 1883 to 1903). One of the main instruments of Khuen's policy were the "Hungarian Royal State Railways" (Magyar kiraly állam vasutak) whose official language was Hungarian, and in that same period from 1878 to 1910 Vinkovci became an important railway hub. Regarding Jews, during the entire period of the Military Frontier in the 18th and 19th century until its demilitarization in 1873, on its territory, they did not have the right to settle permanently, or, they were allowed to spend 24 hours at most on its territory. So the intense inflow of Jews to Vinkovci is actually limited to a relatively short period of the last quarter of the 19th and the beginning of the 20th century, and as a community, they played a relatively significant role in the development of industry and trade, and appropriately, in the development of the civic society in Vinkovci until the beginning of World War II. This colourful identity-ethnic image of Vinkovci was partly the result of the political-social legacy of the Military Frontier, in which Vinkovci was a relatively significant place of military and civil administration, education, handicraft and trade, and partly the result of that Vinkovci economic-demographic conjuncture caused primarily by the demilitarization and the incorporation of the Military Frontier in 1873 and 1881, the coming of the railway to Vinkovci in 1878 and the beginning of intense exploitation of Slavonian forests in that period.

At the end of the 19th century and the beginning of the 20th, an array of the civilian, charitable and cultural societies and clubs was being founded in Vinkovci, and the weekly newspaper (Vinkovci and the Surroundings - Vinkovce und Umgebung) was being regularly published, which was too the indication of the rise of an urban and civic environment, although Vinkovci would only receive the final confirmation of its status of a city as part of a new state in 1923.

The process of industrialization and modernization continued strongly in Vinkovci even after the hard tribulations of World War I, and so in 1919 Vinkovci received its first gas lamp lighting, in 1930 the public electricity grid, and several strong industrial plants operated there (for instance, the Kuman and Bohn and Kuman brickworks; "Brothers Marton" tannery; "Ferolim" metal industry; textile Industry "Wool Clothing Factory Johan Stefan" - later known as "Vinteks", and others).

Just before World War II, Vinkovci reached over 16,000 inhabitants. The War brought new hardships for Vinkovci. By 1942 Vinkovci lost 5% of its population, namely Jews, most of whom were transferred to concentration camps from which they never came back. Most of the members of the other Vinkovci ethnic group, which just like the Jews had greatly contributed to the economic and social development of Vinkovci - the Germans - left Vinkovci in 1944. At the same time, Vinkovci experienced several intensive Allied bombings, particularly in the railway station area.

Vinkovci saw the end of World War II with the loss of at least 35-40% of its pre-war population.