The winning New York Numbers numbers for September 14, 1999 were: evening 2-8-9.
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 |
|---|---|---|---|---|
| Sep 14, 1999 | Evening | 2-8-9 | 19 | 1 |
| Sep 13, 1999 | Evening | 5-8-7 | 20 | 2 |
| Sep 12, 1999 | Evening | 4-7-2 | 13 | 4 |
| Sep 11, 1999 | Evening | 8-1-1 | 10 | 1 |
| Sep 10, 1999 | Evening | 6-5-9 | 20 | 2 |
| Sep 9, 1999 | Evening | 4-7-3 | 14 | 5 |
| Sep 8, 1999 | Evening | 4-0-9 | 13 | 4 |