As a noun, "fraudulent action, a cheat," by 1914. Gypsy's abbreviated form Gip, Gyp is attested from 1840. Gypping or gipping was a term late 19c. among horse dealers for tricks such as painting the animal's gray hairs brown, puffing the gums, etc. Related: Gypped.
mid-15c., "to foam, to froth," from cream (n.). From 1610s in figurative sense of "remove the best part of." Meaning "to beat, thrash, wreck" is 1929, U.S. slang; the exact sense connection is unclear. There was a slang cream (v.) in the 1920s that meant "cheat, deceive, especially by guile." Related: Creamed; creaming.
1590s, "commotion, trouble" (a sense now obsolete), from do (v.). From 1630s as "act of doing;" by 1824 as "something done in a set or formal manner;" by 1835 as "a cheat, a swindle." Phrase do's and dont's "things that out and ought not to be done" (variously apostrophed) is by 1899.
c. 1500, "to break, cut, gouge, etc. with a chisel," from chisel (n.). Slang sense of "to cheat, defraud" is first recorded in 1808 as chizzel; origin and connection to the older word are obscure (but compare slang sense of gouge; perhaps the sense is "to cut close" as in a bargain). Related: Chiseled; chiseling.