The following extract from the Parliamentary Papers in the House of Commons Library may be of interest. It is from ‘Coms. of Inquiry into Charities in England and Wales: Eighteenth Report’ dated 1828. pp.33-34.
https://parlipapers.proquest.com/parlipapers/docview/t70.d75.1828-010968 – but you need a subscription to view it.

It implies that the pub was built by/for Samuel Allen sometime before 1788. Whilst that date appears to match the date that you have him listed as landlord, it raises a question about the preceding 150+ years. Could it have been rebuilt on the site of an earlier pub maybe?

ROBERT DALE’S CHARITY
An annual sum of 40s. is received for the use of the poor of this chapelry,
one moiety thereof by the overseer of the township of Chelmorton, and the
other moiety by the overseer of Flagg, in respect of a public-house in Chelmorton,
called The Duke of York, and lands thereto adjoining.
We were unable at the time of our inquiry to obtain any satisfactory infor
mation as to the origin of this payment; but we have since met with the will
of ROBERT DALE, bearing date 23d August 1742, and proved at Lichfield in
1751, whereby he gave to the poor of Flagg and Chelmorton 40l.; to be invested
on landed security, in three trustees, of whom the parson, for the time being,
of Chelmorton, should be one, to be divided at Christmas or Candlemas; and
when any of the trustees should die, the survivors to choose another out of the
honest and substantial inhabitants. There is a tradition in the chapelry, that
a sum of 40l., belonging to the poor (which probably was derived from Robert
Dale’s legacy) was, with an addition from some other quarter, laid out more
than 40 years ago, in the names of the late Mr. John Buxton, and two other
persons, as trustees, in the purchase of a parcel of land containing between three
and four acres, called The Salt Crofts; that this land adjoined to the common,
a part of which, to the extent of ten acres, or more, was afterwards inclosed and
added to the land thus purchased; that the whole was granted, by the persons
in whose names the purchase was made, to Samuel Allen, on a building lease,
for a very long term of years, at the yearly rent of about 8l. per annum, and
that the above-mentioned public-house was erected thereon; that the rent was
received by the late Mr. Buxton, and divided between the respective overseers
of Chelmorton and Flagg, but that only 20s. of the share which each of them
received, was distributed to the poor, the residue being carried to their general
accounts with their respective townships; and that in consequence of a sum of
125l. having been advanced about 30 years ago, by Mr. Buxton, for paying the
expenses arising from a dispute on the Taddington Inclosure, in which the in-
habitants of Chelmorton and Flagg were interested, Mr. Buxton was allowed
to retain as the interest of the sum thus advanced, the residue of the rents
beyond the two annual sums of 20s. above mentioned.
We are also informed, that Samuel Allen sold his lease to a Mr. Longsden,
and that it is now vested in the daughters of the latter; that the public-house
and the adjoining land are in the occupation of Anne Needham, as tenant
to the Miss Longsdens, who pay the rent reserved by the above-mentioned
lease to the Rev. William Marsden, of Manchester, one of the nephews of
the late Mr. Buxton; and that the two annual sums of 20s. each, are paid over
by him to the overseers, the residue being retained by him as the interest of the
money advanced by the late Mr. Buxton.
The two annual sums of 20s. each are distributed, shortly after they are
received, in small portions, amongst poor persons of the respective townships
of Chelmorton and Flagg.