1560s, "to stand in front of, be facing," from French confronter (15c.), from Medieval Latin confrontare "assign limits to; adjoin," and confrontari "be contiguous to," from assimilated form of Latin com "with, together" (see con-) + frontem (nominative frons) "forehead" (see front (n.)).
Sense of "to face in defiance or hostility, stand in direct opposition to" is from 1580s. Transitive sense of "bring face to face" (with another, the evidence, etc.) is from 1620s. Related: Confronted; confronting.
c. 1300, "to meet as an adversary," from Old French encontrer "meet, come across; confront, fight, oppose," from encontre "a meeting; a fight; opportunity" (12c.), noun use of preposition/adverb encontre "against, counter to" from Late Latin incontra "in front of," from Latin in-"in" (from PIE root *en "in") + contra "against" (see contra). Weakened sense of "meet casually or unexpectedly" first recorded in English early 16c. Related: Encountered; encountering.