Etymology
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penny (n.)

English coin, Middle English peni, from Old English pening, penig, Northumbrian penning "penny," from Proto-Germanic *panninga- (source also of Old Norse penningr, Swedish pänning, Danish penge, Old Frisian panning, Old Saxon pending, Middle Dutch pennic, Dutch penning, Old High German pfenning, German Pfennig, not recorded in Gothic where skatts is used instead), a word of unknown origin.

Offa's reformed coinage on light, broad flans is likely to have begun c.760-5 in London, with an awareness of developments in Francia and East Anglia. ... The broad flan penny established by Offa remained the principal denomination, with only minor changes, until the fourteenth century. [Anna Gannon, "The Iconography of Early Anglo-Saxon Coinage," Oxford, 2003]

The English coin was originally set at one-twelfth of a shilling (or 240 to a Tower pound) and was of silver, later copper, then bronze. There are two plural forms: pennies of individual coins, pence collectively. In Middle English, any coin could be called a penny, and in translations it rendered various foreign coins of small denomination, especially Latin denarius, whence comes its abbreviation d.

As an American English colloquial for cent, it is recorded by 1889. In reference to nails, "a pound," denoting that 1,000 nails will weigh so much, OED says it probably is based originally on the price per 100 and persisted as prices fell.

Penny-a-liner "writer for a journal or newspaper" is attested by 1830, from their supposed rate of pay. Penny dreadful in reference to "cheap and gory fiction" dates from 1870. Phrase penny-wise and pound-foolish is recorded from c. 1600.

Penny-pincher "miserly person" is recorded from 1906 (Middle English had pinchpenny (n.) in that sense; as an adjective penny-pinching is recorded from 1858, American English). Penny loafers attested from 1960, perhaps from the fashion of slipping a penny into the slits of the bands across the facing.

"A regular penny-a-liner is a person who supplies the newspapers of the city with short articles of news, ingenious remarks upon the current topics of the day, reports of meetings, or of cases in the police offices, accidents, &c. &c., but who, observe, has no express engagement from, or any direct connexion with, any newspaper whatever. His success is wholly precarious—always uncertain. If the contributions which those persons forward for publication, in this way, are published, they are certain of payment for them at the rate of one penny, three half-pence, and in rare cases, two pence a-line, according to the importance of the subject matter supplied. ["The London Penny-a-Line System," Irish Monthly Magazine, January 1833]
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penny-ante (adj.)
"cheap, trivial," 1935; extended from use in reference to poker played for insignificant stakes (1855), from penny + ante.
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pennyweight (n.)

unit of measure equal to the weight of one penny, Old English penega gewiht, originally the weight of a silver penny (22 grains); see penny + weight (n.).

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pennyfarthing (adj.)

also penny farthing, penny-farthing, "ineffective," 1887, from penny + farthing, the two together making but a small sum. The noun, in reference to the kind of bicycle with a small wheel in back and a big one in front (so called from the notion of different size coins) is attested by 1920.

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pennyworth (n.)

"goods costing a penny, as much as can be bought for a penny," Middle English peni-worth, from Old English peningwurð; see penny + worth (adj.). Figurative of "small amount" from mid-14c. Also generally, "value for the money given" (mid-14c.).

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penniless (adj.)

"destitute, poverty-stricken," early 14c., penyles, from penny + -less.

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halfpenny (n.)
mid-13c. (though implied in Old English healfpenigwurð "halfpenny-worth"); see half + penny.
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fippeny 
1802, short for five penny; further contracted form fip attested by 1822.
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denier (n.1)

medieval French silver coin corresponding to the English penny, early 15c., from Old French dener, a small coin of slight value, roughly equivalent to the English penny, in use in France from the time of Charlemagne to early modern times, from Latin denarium, from denarius, name of a Roman coin (source also of Spanish dinero); see denarius.

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pringle (n.)

"small silver coin of about the value of a penny," formerly current in Scotland and northern England, 1680s, a word of unknown origin.

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