The winning New York Win 4 numbers for December 22, 1999 were: evening 5-5-8-1.
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 |
|---|---|---|---|---|
| Dec 22, 1999 | Evening | 5-5-8-1 | 19 | 1 |
| Dec 21, 1999 | Evening | 6-1-1-3 | 11 | 2 |
| Dec 20, 1999 | Evening | 2-1-5-2 | 10 | 1 |
| Dec 19, 1999 | Evening | 2-7-3-1 | 13 | 4 |
| Dec 18, 1999 | Evening | 0-3-7-4 | 14 | 5 |
| Dec 17, 1999 | Evening | 9-4-3-3 | 19 | 1 |
| Dec 16, 1999 | Evening | 1-8-8-8 | 25 | 7 |