| Dickey Simpkins Tips 1999-2000 | Stats Glossary  |
| Games with .492 or more Free-throws percentage | Chicago Bulls Record : 9 - 23 | Dickey Simpkins |
| No | Date | Game | Res | Score | Free-throws percentage |
| 1 | Apr 4 | at Milwaukee | L | 73-92 | .667 |
| 2 | Mar 30 | at Miami | L | 80-105 | .500 |
| 3 | Mar 26 | at Houston | L | 78-123 | 1.00 |
| 4 | Mar 24 | vs Denver | W | 70-68 | .500 |
| 5 | Mar 20 | vs Orlando | L | 86-88 | .750 |
| 6 | Mar 18 | at Washington | L | 88-101 | .500 |
| 7 | Mar 15 | at Charlotte | L | 74-77 | .500 |
| 8 | Mar 10 | at Boston | L | 74-104 | .750 |
| 9 | Mar 7 | vs Atlanta | W | 89-82 | .500 |
| 10 | Mar 2 | vs Cleveland | L | 110-114 | 1.00 |
| 11 | Feb 24 | at Indiana | L | 83-100 | 1.00 |
| 12 | Feb 22 | vs Vancouver | L | 81-85 | .500 |
| 13 | Feb 17 | vs Miami | W | 83-76 | .500 |
| 14 | Feb 15 | vs L.A.Lakers | L | 76-88 | 1.00 |
| 15 | Feb 6 | at L.A.Clippers | W | 100-90 | .667 |
| 16 | Feb 1 | at Portland | L | 81-92 | .500 |
| 17 | Jan 28 | vs Sacramento | L | 90-102 | .500 |
| 18 | Jan 25 | at Atlanta | L | 89-96 | .750 |
| 19 | Jan 24 | vs Indiana | W | 83-82 | .500 |
| 20 | Jan 22 | vs Detroit | W | 98-92 | .600 |
| 21 | Jan 18 | at Miami | W | 92-85 | .500 |
| 22 | Jan 8 | vs Boston | W | 96-79 | .500 |
| 23 | Dec 29 | vs Detroit | L | 77-91 | .500 |
| 24 | Dec 27 | vs Indiana | L | 91-103 | 1.00 |
| 25 | Dec 22 | vs Minnesota | L | 86-106 | .500 |
| 26 | Dec 20 | vs Seattle | L | 84-93 | 1.00 |
| 27 | Dec 18 | vs Orlando | L | 74-83 | 1.00 |
| 28 | Dec 4 | vs Milwaukee | L | 91-92 | .500 |
| 29 | Nov 16 | at Golden_State | L | 79-99 | .667 |
| 30 | Nov 13 | vs Boston | W | 92-91 | .500 |
| 31 | Nov 5 | vs Miami | L | 87-105 | .500 |
| 32 | Nov 3 | vs New_York | L | 74-84 | .700 |
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