pit your wits against someone
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.
pit your wits against someoneBRITISH
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.