1909, "with one side facing," from side (n.) + on (adv.), perhaps based on earlier head-on. In reference to a vehicle collision, by 1828.
Entries linking to side-on
side n.
Old English side "flanks of a person, the long part or aspect of anything," from Proto-Germanic *sīdō (source also of Old Saxon sida, Old Norse siða, "flank; side (of meat); coast," Danish side, Swedish sida, Middle Dutch side, Dutch zidje, Old High German sita, German Seite), from adjective *sithas "long" (source of Old English sid "long, broad, spacious," Old Norse siðr "long, hanging down"), from PIE root *se- "long; late" (see soiree).
The "long part of anything" sense is preserved hillside, it also was in 16c.-17c. side-coat "long coat." From 14c. as "lateral half of the body of a slaughtered animal." In reference to bacon, it indicates position relative to the ribs. The meaning "a region, district" is from c. 1400, as in South Side, countryside.
The figurative sense of "position or attitude of a person or set of persons in relation to another" (as in choose sides, side of the story) is recorded by mid-13c. As "an aspect" of anything immaterial (the bright side, etc.), by mid-15c.
The meaning "one of the parties in a transaction" is from late 14c.. The sense of "one of the parties in a sporting contest or game" is from 1690s. The meaning "music on one side of a phonograph record" is attested by 1936. As short for side-dish, by 1848.
The phrase side by side "close together and abreast, placed with sides near together" is recorded from c. 1200. Colloquial on the side "in addition," especially "unacknowledged," with connotations of "illicit, shady," is by 1893.
on prep., adv.
"in a position above and in contact with; in such a position as to be supported by;" also noting the goal to which some action is or has been directed; "about, concerning, regarding; in a position to cover;" as an adverb, "in or into a position in contact with and supported by the top or upper part of something; in or into place; in place for use or action; into movement or action; in operation," Old English on, unstressed variant of an "in, on, into," from Proto-Germanic *ana "on" (source also of Dutch aan, German an, Gothic ana "on, upon"), from PIE root *an- (1) "on" (source also of Avestan ana "on," Greek ana "on, upon," Latin an-, Old Church Slavonic na, Lithuanian nuo "down from").
Also used in Old English in many places where we now would use in. From 16c.-18c. (and still in northern England dialect) often reduced to o'. Phrase on to "aware" is from 1877.