The winning New York Win 4 numbers for September 16, 1999 were: evening 9-9-4-5.
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 16, 1999 | Evening | 9-9-4-5 | 27 | 9 |
| Sep 15, 1999 | Evening | 9-8-6-5 | 28 | 1 |
| Sep 14, 1999 | Evening | 8-7-7-3 | 25 | 7 |
| Sep 13, 1999 | Evening | 9-8-7-0 | 24 | 6 |
| Sep 12, 1999 | Evening | 5-4-0-9 | 18 | 9 |
| Sep 11, 1999 | Evening | 2-6-5-3 | 16 | 7 |
| Sep 10, 1999 | Evening | 5-9-9-4 | 27 | 9 |