Chess, the famous game. Fascinatingly, it is mentioned in the gemara where it says ונדרשיר, one who plays chess.
Kesubos 61b.
Chess is also mentioned by R' Yehuda Halevi in the Kuzari at the end of the fifth essay:
“For this reason, the weak-minded person is unable to beat the strong-minded person in chess. One cannot argue that good or bad luck are factors in the war of chess. This is because all the causes for a victory in chess are within the individual. The wise player will therefore win...”
Kuzari 5:20:52.
The son-in-law of R' Yehuda Halevi, R' Avraham Ibn Ezra (1089-1167), a fervent chess player, wrote several poems about chess. In one of his poems, he describes the rules of the game and the movement options for each piece in the game. Certain rules in modern chess are based on the writings of the Ibn Ezra.
R' Chaim Benveniste (1603-1673) in his Knesses Hagdola writes that he heard that when his rebbe, the Maharit, saw two people playing chess, he would teach them what moves to make. He adds that he also heard that the Mahari Bassan himself also plays chess.
There is a sefer called Maadanei Melech that teaches the rules of chess. This sefer was published in the year 1726 in Frankfurt by the tremendous Torah scholar R' Asher Anshel Worms (1695-1759). In the introduction to the sefer he writes that he published this sefer because he was desperate for money.
What is the origin of the game of chess?
R' Dovid Chaim Korinaldi (1700-1770) in his sefer Beis Dovid cites a source stating that the game of chess was discovered in the possession of an army general who lived before the era of the sages of the mishna. He concludes that it is therefore not surprising that chess is mentioned in the gemara.