| Dickey Simpkins Rankings 1999-2000 | Stats Glossary  |
| Games with 5 or more Points | Chicago Bulls Record : 4 - 23 | Dickey Simpkins |
| No | Date | Game | Res | Score | Points |
| 1 | Mar 30 | at Miami | L | 80-105 | 5 |
| 2 | Mar 20 | vs Orlando | L | 86-88 | 7 |
| 3 | Mar 15 | at Charlotte | L | 74-77 | 7 |
| 4 | Mar 5 | at Charlotte | L | 94-100 | 6 |
| 5 | Mar 2 | vs Cleveland | L | 110-114 | 7 |
| 6 | Feb 25 | vs San_Antonio | L | 78-91 | 9 |
| 7 | Feb 24 | at Indiana | L | 83-100 | 5 |
| 8 | Feb 22 | vs Vancouver | L | 81-85 | 5 |
| 9 | Feb 15 | vs L.A.Lakers | L | 76-88 | 10 |
| 10 | Feb 2 | at Seattle | W | 88-81 | 6 |
| 11 | Feb 1 | at Portland | L | 81-92 | 5 |
| 12 | Jan 25 | at Atlanta | L | 89-96 | 5 |
| 13 | Jan 22 | vs Detroit | W | 98-92 | 9 |
| 14 | Jan 7 | at Washington | W | 110-103 | 8 |
| 15 | Jan 5 | vs Washington | W | 77-66 | 6 |
| 16 | Dec 27 | vs Indiana | L | 91-103 | 10 |
| 17 | Dec 26 | at New_Jersey | L | 76-103 | 10 |
| 18 | Dec 22 | vs Minnesota | L | 86-106 | 7 |
| 19 | Dec 20 | vs Seattle | L | 84-93 | 6 |
| 20 | Dec 18 | vs Orlando | L | 74-83 | 6 |
| 21 | Dec 17 | at Philadelphia | L | 74-77 | 10 |
| 22 | Dec 8 | at Cleveland | L | 93-107 | 6 |
| 23 | Dec 4 | vs Milwaukee | L | 91-92 | 6 |
| 24 | Dec 2 | vs Dallas | L | 95-101 | 5 |
| 25 | Nov 27 | at Dallas | L | 83-95 | 10 |
| 26 | Nov 16 | at Golden_State | L | 79-99 | 6 |
| 27 | Nov 3 | vs New_York | L | 74-84 | 17 |
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