| # | Children | Name | Born | Died | Father | Mother |
| 1 | | | b. 1790 | d. 1837 | David Pickens Gillespie, Sr | Mary Margaret Calhoun |
| 2 | | | b. 1792 | d. 1837 | David Pickens Gillespie, Sr | Mary Margaret Calhoun |
| 3 | | | b. 1795 | d. 1860 | David Pickens Gillespie, Sr | Mary Margaret Calhoun |
| 4 | | | b. 1795 | d. 1865 | David Pickens Gillespie, Sr | Mary Margaret Calhoun |
| 5 | | | b. 1796 | | David Pickens Gillespie, Sr | Mary Margaret Calhoun |
| 6 | | | b. 1800 | d. 1858 | David Pickens Gillespie, Sr | Mary Margaret Calhoun |
| 7 | | | b. 1804 | d. 1837 | David Pickens Gillespie, Sr | Mary Margaret Calhoun |
| 8 | | | b. 22 Nov 1811 | d. 1863 | David Pickens Gillespie, Sr | Mary Margaret Calhoun |
| 9 | | | b. 1814 | d. 1876 | David Pickens Gillespie, Sr | Mary Margaret Calhoun |
| 10 | Yes | | b. 1815 | d. 26 Nov 1866 | David Pickens Gillespie, Sr | Mary Margaret Calhoun |
| 11 | | | b. 1819 | d. 1901 | David Pickens Gillespie, Sr | Mary Margaret Calhoun |