'head-to-head' originates from English, specifically the words 'head' and 'to', where 'head' comes from Old English 'heafod' meaning 'top, front, or the head of the body' and 'to' is the preposition linking the two words.

'head-to-head' changed from the literal physical image of two 'heads' placed 'to' (against) each other to a figurative expression meaning direct confrontation or comparison; the figurative use developed in modern English (19th–20th century) to describe contests and comparisons.

Initially, the phrase conveyed a literal image of 'heads' being near each other; over time it evolved into the current meaning of 'direct confrontation or direct competition'.