James married Rachel Loula Riddle on 14 Dec 1890 in By Rev. B.B. Riddle, Yancey Co., North Carolina. Rachel (daughter of Robert Riddle and Sophronia Burleson) was born on 3 Jan 1871 in North Carolina, USA; died on 17 Apr 1910 in Wellington, Weld Co., Colorado; was buried in Riddle Cemetery, Pensacola, Yancey Co., North Carolina. [Group Sheet] [Family Chart]

1. Clyde F. Dillingham was born on 1 Apr 1893 in Democrat, Buncombe Co., North Carolina; died in 1969.
2. Robert A. Dillingham was born on 6 Dec 1895 in Democrat, Buncombe Co., North Carolina; died on 28 Oct 1896; was buried in Antioch Cemetery, Democrat, Buncombe Co., North Carolina.
3. Matt Stephen Dillingham was born on 16 Sep 1896 in Democrat, Buncombe Co., North Carolina; died on 25 Jul 1969 in Durham, Durham Co., North Carolina; was buried in West Memorial Park Cemetery, Weaverville, Madison Co., North Carolina.
4. Harold Winton Dillingham was born on 7 Nov 1898 in Democrat, Buncombe Co., North Carolina; died on 9 Nov 1967; was buried in Antioch Cemetery, Democrat, Buncombe Co., North Carolina.
5. William Bradley Dillingham
6. Harris Lee Dillingham was born on 16 Feb 1904 in Democrat, Buncombe Co., North Carolina; died on 2 Jan 1968 in Asheville, Buncombe Co., North Carolina.
7. Lula James Dillingham
8. Samuel Riddle Dillingham was born on 24 Oct 1907 in Democrat, Buncombe Co., North Carolina; died on 6 Oct 1976 in Chicago, Illinois, USA.