The winning New York Numbers numbers for October 16, 1999 were: evening 7-7-8.
Sum is the digits added together (5+5+0 = 10). Root sum keeps adding until one digit is left (10 → 1+0 = 1) — many regular players track it in their notebooks. Odd/Even marks each digit O or E (5-5-0 = OOE). High/Low marks 0–4 as L and 5–9 as H (5-5-0 = HHL).
| Date | Draw | Numbers | Sum | Root |
|---|---|---|---|---|
| Oct 16, 1999 | Evening | 7-7-8 | 22 | 4 |
| Oct 15, 1999 | Evening | 4-0-4 | 8 | 8 |
| Oct 14, 1999 | Evening | 4-8-7 | 19 | 1 |
| Oct 13, 1999 | Evening | 6-0-0 | 6 | 6 |
| Oct 12, 1999 | Evening | 3-2-4 | 9 | 9 |
| Oct 11, 1999 | Evening | 9-7-5 | 21 | 3 |
| Oct 10, 1999 | Evening | 0-9-9 | 18 | 9 |