The Roman Empire governed these areas until its collapse in 476 A.D.[2] Kupres was first mentioned in documents from the Kingdom of Croatia, which was based in nearby Duvno (now called Tomislavgrad).

The town is situated in the middle of the Kupres Plain (Kupreško Polje), which has a high strategic importance because of its control of traffic communication between Dalmatia and Central Bosnia.

That made Kupres important in previous wars, which is shown in a famous saying: "Whoever holds this high plain can negotiate with its enemies in any way he wishes.

Kupres was the scene of fierce fighting in the recent War in Bosnia and Herzegovina in the 1990s, leaving the town extensively damaged and the local economy in ruins.

The Battle was fought between the Bosnian Croat Territorial Defence Force (Teritorijalna obrana – TO) supported by the Croatian Army (Hrvatska vojska – HV) troops on one side and the Yugoslav People's Army (Jugoslovenska narodna armija – JNA), supported by the Bosnian Serb TO on the other at the Kupres Plateau, on 3–11 April 1992.

The following year, Croatian authorities charged 21 former JNA members with war crimes against HVO prisoners captured at the Kupres Plateau.

It marks the first tangible evidence of the Bosniak–Croat alliance set out in the Washington Agreement of March 1994, brokered by the United States to end the Croat–Bosniak War fought between the ARBiH and the HVO in Bosnia and Herzegovina.

The town of Kupres has a Roman Catholic church in the parish of the Holy Family and the Ahmed Fazil Paša mosque.

[7] Since 2020, the custom of the grass mowing competition in Kupres ("Strljanica") is inscribed as a UNESCO Intangible Cultural Heritage of Humanity.

Individuals from all ethnic and religious groups in Kupres are free to participate, with the custom being considered as a foundation of the area’s cultural identity, regardless of the people’s background.

Kupres is also famous for its active tourism that doesn't include skiing, like motocross, paragliding, horse riding and off-road driving.

The town also has a large natural lake called the "Kukavičko jezero" Kupres is twinned with:[10][11] Una-Sana  Central Bosnia Posavina  Herzegovina-Neretva Tuzla  West Herzegovina Zenica-Doboj  Sarajevo Bosnian Podrinje Canton 10