There seems to be some disagreement on the ancestry of Henry Dingley, Esq. (d.1589). His father was John and his grandfather was William. This comes from Wolmer v Dyngley, 1538-44, (C 1/1082/30) in which John Wolmer complains to Henry Dingley, requesting the repayment of money he had paid to William Dyngley, deceased, for the marriage of his son John Wolmer (I think) to William's daughter. The original record describes Henry as the son of John Dyngley, Esquire, son of William Dyngley.
John Dyngley, Esq., may have died in 1541/2 (C 142/64/103) but this record doesn't name Henry. William may have died in 1515/6 (C 142/79/170). His wife was Alice, daughter of John Hardwick of Lindley, Leicestershire, by his first wife. John had more daughters with his second wife: Dorothy, Mary, Anne, Joyce, and Elizabeth (in no particular order) (C 1/301/2 and C 142/29/37).
As for the ancestors of William Dyngley, there are several different pedigrees given by various sources. The Visitation of Worcestershire, 1569, gives the following line:
Richard Dyneley m. Eleanor Handsacre
Thomas Dyneley m. ..... Throckmorton/Throgmerton
Richard Dyneley m. Margarett Tracye
William Dyneley m. Alice Hardwick
E.A.B. Barnard in 'The Dingleys of Charlton, Co. Worcester' gives this line (note the inclusion of an extra generation):
Richard Dingley m. Eleanor Handsacre
Thomas Dingley m. ..... Throckmorton
Richard Dingley
Richard Dingley
William Dingley m. Alice Hardwick
I can't find anything on William's parents for certain but did find this: C 139/26/50. It is the proof of age of Thomas Dyneley from 1426/7. The original document begins "Thomas Dyneley fil Willi fil Alianore (sister of) Elizabeth (wife of) Peter Melbourn". The Eleanor I believe refers to Eleanor Handsacre, wife of Richard Dingley, but Richard isn't named. None of the pedigrees mention William but both give Thomas as Richard's son. Barnard states that Richard and Eleanor had married by 1383/4. If Thomas had come of age about 1426 then he would have been born probably around 1405. This seems to be too late to have been Richard and Eleanor's son but would fit to be their grandson via this William. I think this is the same Thomas who appears in this charter of 1434 regarding lands in Charlton (705:134/1531/76/25) and maybe here (E 153/1938). To have come into possession of Charlton, William must have been a descendent of Thomas.
Francis Dingley's tomb of 1624 states that he "deriu(ed) his masculine line from ... the Dineleys ... Ennobled by many ... matches as of Huntaker (Handsacre?) deduced from the ancient Kinges of Scotland, Throgmortn Rowse of Ragley, Tracye Hardwick St Nicolas, Neuell, & Bigge". These seem to all be in order (Francis married a Bigge, his father Henry married (supposedly) a Neville, etc, John married a St Nicholas, etc). This seems to suggest five generations (inclusive) between Richard and William Dingley which agrees with Barnard. Strangely, either Barnard nor the Visitation make mention of the Rowse family of Ragley. Based on this I think William was the grandson of Thomas Dingley (c.1405-?) via an unknown son (potentially Richard if the Barnard and the Visitations are to be trusted). (EDIT: british-history.ac.uk in their page for Cropthorne cites a source (though I couldn't locate the original) stating that in 1484-5 "Sir William (Gascoigne) brought an action against Robert Throckmorton and John Hardwyk on a 'plea why they took away William Dineley a minor,' son and heir of William Dineley, who had been seised of the manor of Charlton". While the only evidence for Richard is the Visitation, this contemporary source would suggest this man's name was actually William.) It seems to me that it was actually more likely that it was William who married a Throckmorton, then Thomas who married a Rowse, his son married a Tracye, and then his son William married Alice Hardwick.
It may instead be that there was another Thomas, another son of Richard Dingley, and his line is correctly given by Barnard. I am not sure how likely this is based on the above, but I am by no means an expert. This is my best guess at how the line should go:
(Richard?) Dyngley m. Eleanor (Handsacre?)
William Dyngley m. ..... Throckmorton
Thomas Dyngley m. ..... Rowse, of Ragley
(EDIT: William?) Dyngley m. ..... Tracye
William Dyngley m. Alice Hardwick, daughter of John Hardwick of Lindley, Leicestershire
John Dyngley m. Elizabeth St Nicholas, daughter of Roger St Nicholas of Thanet, Kent
Henry Dingley m. (Mary Neville?)
Francis Dingley m. 1575 Elizabeth Bigge, daughter of Thomas Bigge of Lenchwick, Worcestershire
It would be great to hear from anyone else researching this family to compare our research.
Thanks!