Lower, Mark A (1860) Patronymica Britannica: a dictionary of the family names of the United Kingdom. London: J.R. Smith. Public Domain.
PENNYMAN
As described in historical dictionaries
Patronymica Britannica (1860)
PENNYMAN. In old Englisli and Scottish, penny was an indefinite designation of money, without respect to its value. See Jamieson. In tlie 'oxVcs., penny -master was the treasurer of a town, society, or corporate bod}', and there are simihir expressions in other languages ; for instance, in Belgium, a treasurer or receiver is known as penningnnaester. Now master and man, though antithetical in one sense, are convertible terms in another, and I am of opinion that Penny-man and Penny-master have one and the same meaning. At any rate, this appears a more rational origin for the name than that assigned in B.L.G. The family, who seem really to be traced only to the year 1599, are asserted to be of Saxon origin ; and the name is said to have been anciently written "Penna-jian, signifying i\\Q chief head man V Peniman. H.R.