| Cleveland Cavaliers Bench Rankings 1999-2000 | Stats Glossary  |
| Games with .741 or higher Free-throws Percentage | Cleveland Cavaliers Record : 20 - 24 |
| No | Date | Game | Score | Free-throws Percentage |
| 1 | Apr 16 | at Atlanta | L | 101-104 | .750 |
| 2 | Apr 15 | vs New_York | W | 106-96 | 1.00 |
| 3 | Apr 10 | at Toronto | L | 103-112 | .857 |
| 4 | Apr 2 | vs Chicago | L | 74-83 | .750 |
| 5 | Apr 1 | vs Boston | W | 109-103 | .833 |
| 6 | Mar 23 | at Dallas | W | 104-98 | .818 |
| 7 | Mar 21 | at Minnesota | L | 107-111 | .800 |
| 8 | Mar 20 | vs Houston | W | 98-85 | 1.00 |
| 9 | Mar 16 | vs Utah | L | 86-107 | .800 |
| 10 | Mar 14 | vs Philadelphia | L | 97-98 | .833 |
| 11 | Mar 7 | at Utah | L | 95-113 | 1.00 |
| 12 | Mar 4 | at L.A.Clippers | W | 109-99 | 1.00 |
| 13 | Feb 23 | vs L.A.Lakers | L | 98-116 | 1.00 |
| 14 | Feb 21 | vs Vancouver | W | 109-108 | 1.00 |
| 15 | Feb 17 | vs Denver | W | 119-101 | .875 |
| 16 | Feb 15 | vs San_Antonio | W | 92-81 | 1.00 |
| 17 | Feb 8 | at Houston | L | 83-91 | 1.00 |
| 18 | Feb 5 | vs Atlanta | L | 94-102 | 1.00 |
| 19 | Feb 4 | at Detroit | L | 96-105 | .857 |
| 20 | Jan 29 | at Washington | L | 98-103 | 1.00 |
| 21 | Jan 27 | vs Orlando | W | 102-90 | .800 |
| 22 | Jan 18 | at Seattle | L | 80-99 | 1.00 |
| 23 | Jan 16 | at Sacramento | L | 102-113 | .750 |
| 24 | Jan 12 | at Portland | L | 75-95 | 1.00 |
| 25 | Jan 8 | at New_York | W | 89-86 | .800 |
| 26 | Jan 6 | vs Golden_State | W | 90-75 | .857 |
| 27 | Jan 4 | vs Sacramento | L | 107-111 | 1.00 |
| 28 | Dec 26 | vs Toronto | L | 95-98 | 1.00 |
| 29 | Dec 20 | vs Minnesota | L | 94-100 | 1.00 |
| 30 | Dec 17 | at Charlotte | L | 86-99 | 1.00 |
| 31 | Dec 14 | vs Boston | W | 115-88 | .909 |
| 32 | Dec 11 | vs Atlanta | W | 127-116 | .900 |
| 33 | Dec 10 | at Indiana | L | 88-136 | .786 |
| 34 | Dec 8 | vs Chicago | W | 107-93 | 1.00 |
| 35 | Dec 3 | vs Philadelphia | L | 100-102 | .750 |
| 36 | Dec 1 | at Washington | W | 111-108 | .786 |
| 37 | Nov 30 | vs Dallas | W | 106-99 | 1.00 |
| 38 | Nov 27 | vs Charlotte | W | 106-89 | .750 |
| 39 | Nov 17 | at Boston | L | 103-114 | .875 |
| 40 | Nov 13 | vs Milwaukee | W | 117-112 | .750 |
| 41 | Nov 11 | vs Seattle | L | 103-109 | .800 |
| 42 | Nov 6 | vs New_York | W | 102-93 | .818 |
| 43 | Nov 5 | at Orlando | W | 104-99 | 1.00 |
| 44 | Nov 2 | at New_York | L | 84-92 | .750 |
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