This saying originated from a Middle English saying, round about 1545 A.D.
A coward verely neuer obteyned the loue of a faire lady.
[1545 R. Taverner tr. Erasmus' Adages (ed. 2) 10]
In 1614 A.D., this was refined to become:
Faint heart neuer wonne faire Lady.
[1614 W. Camden Remains concerning Britain (ed. 2) 306]
And later in 1754A.D., it was phrased in today's recognizable English:
Then, madam, we will not take your denial. ‥Have I not heard it said, that faint heart never won fair lady.
[1754 Richardson Grandison I. xvi.]
Thus is the origin of this saying.
These sayings were taken out of these books.
If you do not wish to browse through all those books for these few phrases, try this site
OED 1 gives the earliest use in an intransitive sense 1. a. ‘To fail. rare.’
1831 Constellation 1 Jan 54/1 It is a common expression in New-England, to say of a person, who does not get a king in the game of chequers, he skunked.
The earliest transitive use given in OED use is 1. b. ‘to defeat or get the better of; to inflict defeat upon.’
In some quots. in passive = ‘defeated without making a score’
OED 1 gives citations with this sense from the 1840s referring to card games, games of chance, and politics.
Alongside this, however, there are transitive uses with the sense cheat. OED 1 gives two:
2. a. To fail to pay (a bill or creditor)
1851 B.H. HallCollege Wods 284 Skunk, at Princeton College, to fail to pay a debt; used actively; e.g., to skunk a tailor, i.e., not to pay him.
b. To cheat; in pass., to be cheated out of
1890 C. W. Haskins Argonauts of Calif. xviii, 250, I got skunked once out of a good claim.
The last construction, however, is at least a hundred years older than the OED citation; the Worcester [Massachusetts] Magazine, III, xii (1787) ,151 has
… the heathen poets firſt invented theſe ſtories, and the heathen prieſts ſtole them from them, as badgers dig holes for themſelves, and afterwards are ſkunked out of them, by the foxes.
What exactly this means is suggested in this, from Mass Audubon, the website of the Massachusetts Audubon Society:
The skunk may excavate its own burrow [...] More often a skunk will take over the burrows of woodchucks or foxes.
So it appears that ‘cheat out of’ is the original sense, and that the sense ‘utterly defeat’ is derivative.
All the earliest citations are from, or attributed to, New England. All except the first are still current.
Best Answer
An initial finding in The News, Frederick, Maryland, 17 Oct 1919 (paywalled),
confirmed that calling a cold wind, or cold weather generally, 'the hawk' or 'Hawkins' was much older than posited at sites such as Wikipedia (1934 in the Baltimore Sun) and DARE (paywalled; citations with additional information at The Big Apple).
An additional finding in "Weather-Lore", by J.H. Evans, originally published in the 1896 Southern Workman, v. 25, p. 16, confirmed that use predated the 20th century among "Afro-Americans" (the article by Evans from Southern Workman is reprinted in the 1983 Strange Ways and Sweet Dreams: Afro-American Folklore from the Hampton Institute). In context, the suggestion is that the use of 'Hawkins is coming' to mean "cold weather is coming" was passed down from the "dark ages of [African-American] slavery".
The original publication date of Evans' "Weather-Lore" was not at first clear from the textual evidence in Strange Ways and Sweet Dreams; the article appeared to have been reprinted from Southern Workman 25, no. 1, January 1896. Evidence in the 1926 Folk beliefs of the southern Negro corroborated that the article is in Southern Workman, v. 25, p. 16: see note 4, page 505 (where the year given, "1895" is an error) and following, e.g., page 511 (where the correct year, "1896", is given), although there the significance of turkeys roosting high has been mysteriously transmuted from cold to rain.