The winning Delaware Play 4 numbers for May 16, 1999 were: night 4-3-5-9.
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 |
|---|---|---|---|---|
| May 16, 1999 | Night | 4-3-5-9 | 21 | 3 |
| May 15, 1999 | Night | 4-7-7-9 | 27 | 9 |
| May 15, 1999 | Day | 0-8-9-7 | 24 | 6 |
| May 14, 1999 | Night | 4-5-6-8 | 23 | 5 |
| May 14, 1999 | Day | 8-5-4-3 | 20 | 2 |
| May 13, 1999 | Night | 4-2-8-1 | 15 | 6 |
| May 13, 1999 | Day | 0-5-4-3 | 12 | 3 |
| May 12, 1999 | Night | 4-6-4-8 | 22 | 4 |
| May 12, 1999 | Day | 0-2-3-0 | 5 | 5 |
| May 11, 1999 | Night | 9-5-0-9 | 23 | 5 |
| May 11, 1999 | Day | 6-9-5-9 | 29 | 2 |
| May 10, 1999 | Night | 2-2-9-5 | 18 | 9 |
| May 10, 1999 | Day | 2-3-0-1 | 6 | 6 |