Handicap Chess

Handicap is a native English formation, recorded as a noun in the 1650s and derived from hand in cap, a wagering game in which two bettors and a neutral umpire settled the odds in an unequal contest by putting hands holding forfeit money into a hat or cap; the custom, though not the name, is attested from the 14th century in Piers Plowman. The word moved to horse racing by 1754 and to the general sense of an encumbrance by 1890. Chess prefers the older term odds, itself attested from about 1500 for unequal things and in the wagering sense from the 1590s. Wikipedia's Odds (chess) article documents the practice as central to 18th and 19th century play: Philidor (1726-1795) played most of his games at odds, Howard Staunton codified odds play in The Chess-Player's Handbook (1847) and The Chess-Player's Companion (1849), and the earliest dated odds game shown there is Harrwitz versus Staunton, 1846. The Glossary of chess carries odds as the headword.

First documented: n.a. for handicap chess as a fixed phrase; odds play documented from the 18th-19th centuries — Howard Staunton, The Chess-Player's Handbook (1847) and The Chess-Player's Companion (1849), per Wikipedia, Odds (chess)