This paper considers in a descriptive way and analyzes in historical, ethnological and linguistic terms the gaming entertainments of the Bessarabian Gagauz associated with intellectual rivalry, ingenuity and prudence. The main source for the work served the publications of the Russian ethnographer V. A. Moshkov, the Romanian historian M. P. Guboglu, the Moldavian folklorists G. A. Gaidarji, S. S. Kuroglo, L. S. Cimpoeș, F. I. Zanet, and the handwritten works of the Moldavian linguists B. P. Tukan, E. K. Colța. In addition, newspaper, magazine and brochure materials of the last decades, as well as electronic publications on this topic, were used. Wherein, special attention was paid to the common name, to particular segments of this or that game entertainment, since these features convey its national specificity. Of great interest is a board game like checkers called kuran (this word refers to a game situation when three game pieces are placed on a special board on one line, which leads to a win; the etymology of the name, in our opinion, goes back to the Arabic word kura meaning “lot”). Another game that requires ingenuity from its participants, called cızık (“burnt”), is played on the ground: two players alternately lay out corn grains in dug holes (each has three) until there are no free grains left; whoever has the most grains wins. Of particular interest are card games that appeared among the Gagauz in the Bessarabian period of their history. Here are just some of their names ‒ Kör durak (“Blind durak”), Domuzçuk (“Piggy”), Soykoz (“One’s trump card”), Keçi (“Goat”), as well as the names of card suits ‒ develi (hearts), pesmetli (diamonds), karalı (spades), kruçalı (clubs). In addition, various puzzle tasks were used as entertainment. In comparative terms, an analysis is made of similar games and entertainments among such peoples as Bulgarians, Moldovans, Romanians, Russians, and Turks.