pit (one's) wits against (someone or something)

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pit (one's) wits against (someone or something)

To engage in a contest of intelligence with someone or something. In the show, five couples will pit their wits against each other to see who knows more pop culture trivia. The best chess player in the world is pitting his wits against a supercomputer.
See also: pit, wit

pit your wits against someone

BRITISH
If you pit your wits against someone, you use your intelligence to try to defeat them. I'm as ambitious as the next man. I'd like to manage a team at the very highest level and pit my wits against the best. He enjoyed pitting his wits against those of the Wall Street analysts.
See also: pit, someone, wit

pit your wits against

compete with someone or something.
1996 Earl Lovelace Salt Michael…would be the one to make money…there was no greater cause or adversary to pit his wits and slickness and spite against.
See also: pit, wit

ˌpit your ˈwits (against somebody/something)

compete with somebody/something in a test of intelligence or knowledge: He’s pitting his wits against the computer chess game.
See also: pit, wit