The winning Vermont Pick 3 numbers for October 23, 1999 were: day 5-3-1.
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 |
|---|---|---|---|---|
| Oct 23, 1999 | Day | 5-3-1 | 9 | 9 |
| Oct 22, 1999 | Day | 5-3-0 | 8 | 8 |
| Oct 21, 1999 | Day | 4-1-2 | 7 | 7 |
| Oct 20, 1999 | Day | 1-8-5 | 14 | 5 |
| Oct 19, 1999 | Day | 8-8-2 | 18 | 9 |
| Oct 18, 1999 | Day | 3-3-1 | 7 | 7 |
| Oct 17, 1999 | Day | 8-9-2 | 19 | 1 |