Old English hol (adj.) "hollow, concave;" as a noun, "hollow place; cave; orifice; perforation," from Proto-Germanic *hulan (source also of Old Saxon, Old Frisian, Old High German hol, Middle Dutch hool, Old Norse holr, German hohl "hollow," Gothic us-hulon "to hollow out"), from PIE root *kel- (1) "to cover, conceal, save." As an adjective, it has been displaced by hollow, which in Old English was only a noun, meaning "excavated habitation of certain wild animals."
As a contemptuous word for "small dingy lodging or abode" it is attested from 1610s. Meaning "a fix, scrape, mess" is from 1760. Obscene slang use for "vulva" is implied from mid-14c. Golfing hole-in-one is from 1914; as a verbal phrase from 1913. To need (something) like a hole in the head, applied to something useless or detrimental, first recorded 1944 in entertainment publications, probably a translation of a Yiddish expression such as ich darf es vi a loch in kop.
Old English up, uppe, from Proto-Germanic *upp- "up" (source also of Old Frisian, Old Saxon up "up, upward," Old Norse upp; Danish, Dutch op; Old High German uf, German auf "up"; Gothic iup "up, upward," uf "on, upon, under;" Old High German oba, German ob "over, above, on, upon"), from PIE root *upo "under," also "up from under," hence also "over."
As a preposition, "to a higher place" from c. 1500; also "along, through" (1510s), "toward" (1590s). Often used elliptically for go up, come up, rise up, etc. Up the river "in jail" first recorded 1891, originally in reference to Sing Sing, which is up the Hudson from New York City. To drive someone up the wall (1951) is from the notion of the behavior of lunatics or caged animals. Insulting retort up yours (scil. ass) is attested by late 19c.
1550s, "to drive and catch (swans)," from up (adv.). Intransitive meaning "get up, rise to one's feet" (as in up and leave) is recorded from 1640s. Sense of "to move upward" is recorded from 1737. Meaning "increase" (as in up the price of oil) is attested from 1915. Compare Old English verb uppian "to rise up, swell." Related: Upped; upping. Upping block, used for mounting or dismounting horses, carriages, etc., is attested from 1796 (earlier was horsing-block, 1660s).