The winning Massachusetts The Numbers Game numbers for May 16, 1999 were: evening 2-4-3-2.
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 |
|---|---|---|---|---|
| May 16, 1999 | Evening | 2-4-3-2 | 11 | 2 |
| May 15, 1999 | Evening | 9-3-1-6 | 19 | 1 |
| May 14, 1999 | Evening | 4-5-2-8 | 19 | 1 |
| May 13, 1999 | Evening | 8-7-9-6 | 30 | 3 |
| May 12, 1999 | Evening | 4-2-9-6 | 21 | 3 |
| May 11, 1999 | Evening | 2-4-3-3 | 12 | 3 |
| May 10, 1999 | Evening | 3-5-8-4 | 20 | 2 |