b. = born
bap. = baptised
c. = christened
c/m = marriage contract
d. = died
d. vita patris = died in the father's lifetime
dsp = (decessit sine prole) died without issue
m. = married
Patrick Monypenny, 1st of Pilrig, is the first for whom there is evidence and although being nearly related to Monypenny of Pitmilly, in Fife, the precise details of the relationship are uncertain. He m. by 6 March 1485, to Ellen, daughter of John Duddingston, (survived him and had her annualrent of Pilrig reserved to her on 5 March 1500), when they had a precept from Robert, Abbot of Holyrood, for their infeftment in the lands of Pilrig on a resignation in their favour by her father. He was witness to a charter by Sir John Logan of Restalrig to the Hospital of Saint Anthony of Leith, on 19 January 1496 and d. by 5 March 1500. He was father of,
Robert Monypenny, 2nd of Pilrig, succeeded his father and was infeft in the lands of Pilrig as heir to him on 5 March 1500. He m. by 14 July 1506, to Margaret Crawford, (she was widow of Archbald Sinclair of Westhall), when they were infeft, jointly, in his lands of Pilrig. They also had conjunct infeftment in the Common Muir on 12 October 1521 and had their liferents of Pilrig reserved to them in their son and heir, Robert Moneypenny’s infeftment in the lands of Pilrig on 23 February 1538. He was father of,
- Robert Monypenny, 3rd of Pilrig, (see below).
- Mr. John Monypenny, had a charter from Robert, Commendator of Holyrood, for the husbandlands belonging to the church within the parish of Gilmerton, on 6 November 1555 which he conveyed to his nephew, Patrick Monypenny of Pilrig, on 14 February 1566-67.
Robert Monypenny, 3rd of Pilrig, was infeft in the lands of Pilrig on 20 January 1510, on his parent’s resignation to him and had a Tack of the teidnsheaves of Pilrig from Robert, Abbot of Holyrood, on 12 November 1531. He m. by 20 October 1531, to Janet Ramsay when they had a charter to them by his mother, Margaret Crawford, for the lands of Over Edmersdene, in the sheriffdom of Berwick, and was infeft in Pilrig on 23 February 1538, with reservation of the liferent to his parents. He had a charter for the lands of Westhall, in the constabulary of Haddington, on 17 December 1540, on a resignation to him by Andrew Rattray of Westhall, and was k. at the battle of Pinkie, in September 1547. He was father of
Patrick Monypenny, 4th of Pilrig, succeeded his father and had Sasine for the lands of Westhall as heir to him on 15 April 1551. He m. by 24 November 1550, to Catherine Kincaid, when they had Sasine for the lands of Pilrig and they a conjunct charter under the Great Seal for those of Parkhill on 1 June 1551. He m. firstly, to the said Catherine Kincaid, and secondly, to Katherine, daughter of Andrew Wood, 2nd of Largo, (c/m 22 August 1562), with whom, on his resignation, he had a conjunct charter for his lands of Westhall on 21 February 1562-63, with reservation to his mother, Janet Ramsay. He m. thirdly, to Euphame Duddingston, (she d. on 29 May 1582) by whom he had issue ; and d. at Glendevon, on 14 November 1605. He was father of,
- Mr. Archibald Monypenny, fiar of Pilrig, (see below).
- Patrick Moneypenny, had the gift of the escheat goods of Mr Alexander Chalmer, Vicar of Barro, on 11 November 1569 and to whom his father conveyed the husbandlands in the parish of Libberton on 16 July 1583. He dsp, his nephew, Patrick Monypenny of Pilrig, being served heir to him in those lands on 18 August 1607.
- Robert Monypenny, to who his father conveyed an annualrent from the lands of Balquhan on 20 March 1583 and had dsp by 29 March 1584 when his father was infeft in that same annualrent as heir to him.
- Patrick Monypenny, who is the only child named in his mother, Euphame Duddingston’s Testament in 1582.
Mr. Archibald Monypenny, fiar of Pilrig, the eldest son, m. by 25 April 1583, to Martha Lundy when they had a conjunct charter for the lands of Westhall, on his father’s resignation. He d. vita patris on 12 April 1602 and was father of,
Sir Patrick Monypenny, 5th of Pilrig and Glendevon, succeeded his grandfather and was served heir general to him on 25 February 1607. He was also served heir to his father, Mr. Archibald, in the lands of Westhall, in the constabulary of Haddington, on 18 August 1608, and to his paternal uncle, Patrick, in chruchlands in Libberton on the same day. He was infeft in the husbandlands in Gilmerton on 11 April 1612, as heir to his grandfather, and m. Elizabeth Hamilton with whom he disponed his lands of Pilrig to Gilbert Kirkwood, Goldsmith and Burgess of Edinburgh, on 13 April 1623. He also disponed his lands of Westhall to Sir James Lundy who had a confirmations for them under the Great Seal, firstly, on 22 July 1623 and again on 3 March 1632, and also disponed those of Glendevon, comprising Easter Glensherop and Whitehills, to William Bonar of Keltie on 18 December 1643.
 Ex. Rolls. Vol. XVIII. P. 513. Which states that he “obiit in campo de Pinkecleuch.”