| Family with parents |
| mother |
Alice Elsey Jane Lightbourn Simons Christening: 9 April 1848 28 Death: 8 April 1904 — Sandys, Bermuda |
| himself |
Sidney Waddington Bennett Birth: 1873 24 Death: 19 June 1874 — Sandys, Bermuda |
|
12 years younger brother |
George Arthur Bennett Birth: 1884 Death: 1 August 1968 — St Georges, Bermuda |
| Mother’s family with Amos Bennett |
| step-father |
Amos Bennett Birth: 1845 |
| mother |
Alice Elsey Jane Lightbourn Simons Christening: 9 April 1848 28 Death: 8 April 1904 — Sandys, Bermuda |
|
Marriage: 5 April 1867 — Sandys, Bermuda |
|
|
1 month half-brother |
James Alfred Bennett Birth: 5 May 1867 22 19 — Ireland Island, Sandys, Bermuda |
|
15 months half-brother |
James Henry Bennett Birth: 29 July 1868 23 20 — Ireland Island, Sandys, Bermuda |
|
2 years half-sister |
Crosby Bennett Birth: 25 September 1870 25 22 — Ireland Island, Sandys, Bermuda Death: 27 March 1897 — Sandys, Bermuda |
|
3 years half-brother |
Charles Alexander Wellington Bennett Christening: 4 March 1874 29 25 — Sandys, Bermuda Death: 19 June 1874 |
|
11 years younger brother |
George Arthur Bennett Birth: 1884 Death: 1 August 1968 — St Georges, Bermuda |
| Mother’s family with William Wilcott |
| step-father | |
| mother |
Alice Elsey Jane Lightbourn Simons Christening: 9 April 1848 28 Death: 8 April 1904 — Sandys, Bermuda |
| half-sister |
Alice Jane Bennett Birth: 1875 26 |
|
5 years half-sister |
Laura Emily Wilcott Bennett Birth: 7 December 1879 31 — Sandys, Bermuda Death: 28 May 1945 |