The winning Massachusetts The Numbers Game numbers for October 19, 1999 were: evening 3-6-8-9.
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 |
|---|---|---|---|---|
| Oct 19, 1999 | Evening | 3-6-8-9 | 26 | 8 |
| Oct 18, 1999 | Evening | 6-2-4-4 | 16 | 7 |
| Oct 17, 1999 | Evening | 5-3-5-8 | 21 | 3 |
| Oct 16, 1999 | Evening | 8-0-1-5 | 14 | 5 |
| Oct 15, 1999 | Evening | 3-9-2-3 | 17 | 8 |
| Oct 14, 1999 | Evening | 1-7-8-6 | 22 | 4 |
| Oct 13, 1999 | Evening | 1-8-5-6 | 20 | 2 |