Valentine married Ann REE on 7 Apr 1655 in Tanderagree, Armagh, Ireland. Ann (daughter of Nicholass WRAY and Ann UNKNOWN) was born about 1628 in Tanderagree, Armagh, Ireland; died on 1 Feb 1671 in Ballyvickcrannel, Sego, Armagh, IRL; was buried about 4 Feb 1671 in Moyraverty, Armagh, Ireland. [Group Sheet] [Family Chart]

1. Mary HOLLINGSWORTH was born on 25 Jan 1657 in Belleniskcrannel, Armagh, IRL; died in 1746.
2. Henry HOLLINGSWORTH was born in 1658 in Belleniskcrannel, Armagh, IRL; died on 12 Mar 1721 in Elkton, Cecil, MD, USA.
3. Thomas HOLLINGSWORTH was born on 1 May 1661 in Sego, Armagh, Ire; died in 2nd da 2nd mo 1727 in Christian Hundred, New Castle, DE, USA.
4. Catherine HOLLINGSWORTH was born in May 1663 in , , , Ireland; died on 29 Jun 1746 in Newark, New Castle, DE.

Valentine married Ann CALVERT on 12 Apr 1672 in Lurgan, Armagh, Ireland. Ann (daughter of Thomas CALVERT and Jane GLASFORD) was born on 9 Nov 1650 in Kilvaring, Down, Ire; died on 17 Aug 1697 in Newark M.M., New Castle, DE, USA; was buried about 18 Aug 1697 in Newark M.M., New Castle, DE, USA. [Group Sheet] [Family Chart]

1. Samuel HOLLINGSWORTH was born on 27 Jan 1673 in Ballyvickcrannel, Sego, Armagh, IRL; died after 30 Aug 1748 in Birmingham Twp., Chester, PA, USA.
2. Enoch HOLLINGSWORTH was born on 7 Jun 1675 in Ballyvickcrannel, Sego, Armagh, IRL; died on 24 Oct 1687 in , New Castle, DE, USA.
3. Valentine HOLLINGSWORTH, Jr. was born on 12 Nov 1677 in Ballyvickcrannel, Sego, Armagh, IRL; died before 25 Mar 1757.
4. Ann HOLLINGSWORTH was born on 28 Oct 1680 in Ballyvickcrannel, Sego, Armagh, IRL; died after 26 Oct 1712 in , Salem, NJ.
5. John HOLLINGSWORTH was born on 19 Feb 1684 in Shellpot Creek, New Castle, DE; died in Aug 1722.
6. Joseph HOLLINGSWORTH was born on 10 May 1686 in Shellpot Creek, New Castle, DE; died about 1732.
7. Enoch HOLLINGSWORTH was born about 1688 in Shellpot Creek, New Castle, DE; died in Sep 1690.

Henry married Katheran UNKNOWN. [Group Sheet] [Family Chart]