Roundhead n.

c. 1300 (early 13c. as a surname), "spherical in shape; circular in outline," of persons or animals, "well-fed;" from Anglo-French rounde, Old French roont (12c., Modern French rond), probably originally *redond, from Vulgar Latin *retundus (source also of Provençal redon, Spanish redondo, Old Italian ritondo), from Latin rotundus "like a wheel, circular, round," related to rota "wheel" (see rotary). The French word is the source of Middle Dutch ront (Dutch rond), Middle High German runt (German rund) and similar words in the Germanic languages. 

As an adverb from c. 1300. As a preposition from c. 1600, "so as to make a complete circuit" (as in round the world); 1715 as "throughout, all through" (as in round the clock); by 1743 as "so as to make a turn or partial circuit about" (as in round the corner). In many cases it is a shortened form of around (adv.).

Of numbers from mid-14c., "entire, full, complete, brought to completion," with the notion of symmetry extended to that of completeness. Round number for one only approximately correct, usually expressed in 10s, 100s, etc., is by 1640s. Compare round (v.). Round trip "an outward and return journey" is by 1844, originally of railways. A round-dance (1520s) is one in which the dancers move in a circle or ring. Round heels attested from 1926, in reference to incompetent boxers, 1927 in reference to loose women, implying in either case a tendency to end up flat on one's back.

Old English heafod "top of the body," also "upper end of a slope," also "chief person, leader, ruler; capital city," from Proto-Germanic *haubid (source also of Old Saxon hobid, Old Norse hofuð, Old Frisian haved, Middle Dutch hovet, Dutch hoofd, Old High German houbit, German Haupt, Gothic haubiþ "head"), from PIE root *kaput- "head."

Modern spelling is early 15c., representing what was then a long vowel (as in heat) and remained after pronunciation shifted. Of rounded tops of plants from late 14c. Meaning "origin of a river" is mid-14c. Meaning "obverse of a coin" (the side with the portrait) is from 1680s; meaning "foam on a mug of beer" is first attested 1540s; meaning "toilet" is from 1748, based on location of crew toilet in the bow (or head) of a ship.

Synechdochic use for "person" (as in head count) is first attested late 13c.; of cattle, etc., in this sense from 1510s. As a height measure of persons, from c. 1300. Meaning "drug addict" (usually in a compound with the preferred drug as the first element) is from 1911.

To be over (one's) head "beyond one's comprehension" is by 1620s. To give head "perform fellatio" is from 1950s. Phrase heads will roll "people will be punished" (1930) translates Adolf Hitler. Head case "eccentric or insane person" is from 1966. Head game "mental manipulation" attested by 1972.