| month | day | visitor | score | home | score |
| November | 2, 1999 | Magic | 96 | Blazers | 107 |
| November | 4, 1999 | Blazers | 116 | Suns | 124 |
| November | 6, 1999 | Clippers | 115 | Blazers | 127 |
| November | 9, 1999 | Blazers | 109 | Nets | 112 |
| November | 13, 1999 | Nets | 104 | Blazers | 120 |
| November | 15, 1999 | Blazers | 125 | Clippers | 119 |
| November | 17, 1999 | Spurs | 93 | Blazers | 124 |
| November | 19, 1999 | Blazers | 117 | Mavericks | 112 |
| November | 22, 1999 | Blazers | 121 | Jazz | 115 |
| November | 26, 1999 | Blazers | 120 | Sonics | 104 |
| November | 28, 1999 | Blazers | 124 | Magic | 106 |
| November | 29, 1999 | Mavericks | 101 | Blazers | 131 |
| November | 30, 1999 | Wolves | 121 | Blazers | 142 |
| December | 1, 1999 | Blazers | 145 | 76ers | 121 |
| December | 2, 1999 | Blazers | 135 | Pistons | 107 |
| December | 3, 1999 | Pacers | 93 | Blazers | 153 |
| December | 5, 1999 | Blazers | 118 | Kings | 123 |
| December | 7, 1999 | Grizzlies | 114 | Blazers | 127 |
| December | 10, 1999 | Suns | 128 | Blazers | 130 |
| December | 12, 1999 | Grizzlies | 99 | Blazers | 110 |
| December | 13, 1999 | Bulls | 106 | Blazers | 145 |
| December | 14, 1999 | Knicks | 98 | Blazers | 123 |
| December | 15, 1999 | Blazers | 126 | Cavaliers | 109 |
| December | 19, 1999 | Blazers | 130 | Bullets | 98 |
| December | 22, 1999 | Blazers | 133 | Spurs | 117 |
| December | 25, 1999 | Blazers | 140 | Lakers | 118 |
| December | 28, 1999 | Bucks | 116 | Blazers | 124 |
| December | 29, 1999 | Blazers | 119 | Kings | 115 |
| January | 4, 2000 | Blazers | 136 | Lakers | 147 |
| January | 5, 2000 | Rockets | 115 | Blazers | 134 |
| January | 7, 2000 | Nuggets | 126 | Blazers | 123 |
| January | 9, 2000 | Wolves | 127 | Blazers | 144 |
| January | 13, 2000 | Blazers | 126 | Wolves | 125 |
| January | 15, 2000 | Blazers | 104 | Pacers | 117 |
| January | 16, 2000 | Bullets | 126 | Blazers | 132 |
| January | 22, 2000 | Cavaliers | 110 | Blazers | 119 |
| January | 23, 2000 | Kings | 96 | Blazers | 114 |
| January | 24, 2000 | Blazers | 137 | Suns | 134 |
| January | 25, 2000 | Blazers | 132 | Rockets | 131 |
| January | 26, 2000 | Kings | 105 | Blazers | 132 |
| January | 27, 2000 | 76ers | 96 | Blazers | 111 |
| January | 30, 2000 | Jazz | 97 | Blazers | 140 |
| January | 31, 2000 | Blazers | 138 | Clippers | 150 |
| February | 1, 2000 | Blazers | 123 | Hawks | 121 |
| February | 2, 2000 | Blazers | 104 | Warriors | 119 |
| February | 4, 2000 | Blazers | 125 | Warriors | 132 |
| February | 8, 2000 | Hornets | 109 | Blazers | 102 |
| February | 11, 2000 | Pistons | 117 | Blazers | 132 |
| February | 14, 2000 | Blazers | 93 | Sonics | 105 |
| February | 16, 2000 | Raptors | 116 | Blazers | 120 |
| February | 17, 2000 | Warriors | 100 | Blazers | 144 |
| February | 18, 2000 | Celtics | 132 | Blazers | 130 |
| February | 19, 2000 | Blazers | 139 | Bulls | 103 |
| February | 20, 2000 | Blazers | 123 | Warriors | 111 |
| February | 25, 2000 | Blazers | 126 | Heat | 121 |
| February | 26, 2000 | Blazers | 136 | Knicks | 119 |
| March | 1, 2000 | Nuggets | 131 | Blazers | 134 |
| March | 2, 2000 | Clippers | 105 | Blazers | 136 |
| March | 5, 2000 | Blazers | 149 | Nuggets | 97 |
| March | 7, 2000 | Blazers | 146 | Jazz | 106 |
| March | 8, 2000 | Jazz | 106 | Blazers | 143 |
| March | 10, 2000 | Hawks | 99 | Blazers | 127 |
| March | 16, 2000 | Rockets | 86 | Blazers | 121 |
| March | 17, 2000 | Blazers | 123 | Grizzlies | 121 |
| March | 19, 2000 | Heat | 114 | Blazers | 110 |
| March | 20, 2000 | Blazers | 148 | Clippers | 90 |
| March | 21, 2000 | Sonics | 98 | Blazers | 131 |
| March | 23, 2000 | Suns | 126 | Blazers | 129 |
| March | 24, 2000 | Blazers | 134 | Suns | 119 |
| March | 25, 2000 | Sonics | 96 | Blazers | 138 |
| March | 27, 2000 | Lakers | 131 | Blazers | 139 |
| March | 28, 2000 | Warriors | 115 | Blazers | 124 |
| March | 30, 2000 | Blazers | 134 | Raptors | 105 |
| April | 3, 2000 | Mavericks | 104 | Blazers | 137 |
| April | 6, 2000 | Blazers | 106 | Hornets | 78 |
| April | 8, 2000 | Blazers | 128 | Bucks | 87 |
| April | 10, 2000 | Spurs | 117 | Blazers | 118 |
| April | 12, 2000 | Lakers | 127 | Blazers | 142 |
| April | 16, 2000 | Blazers | 114 | Kings | 129 |
| April | 17, 2000 | Blazers | 125 | Celtics | 119 |
| April | 22, 2000 | Blazers | 126 | Lakers | 130 |
| April | 23, 2000 | Blazers | 114 | Sonics | 97 |
| Post | 1, 2000 | Rockets | 120 | Blazers | 132 |
| Post | 2, 2000 | Rockets | 104 | Blazers | 134 |
| Post | 3, 2000 | Blazers | 109 | Rockets | 101 |
| Post | 4, 2000 | Blazers | 136 | Rockets | 134 |
| Post | 5, 2000 | Rockets | | Blazers | |
| Post | 6, 2000 | Blazers | | Rockets | |
| Post | 7, 2000 | Rockets | | Blazers | |
| Post | 8, 2000 | Kings | 103 | Blazers | 114 |
| Post | 9, 2000 | Kings | 139 | Blazers | 135 |
| Post | 10, 2000 | Blazers | 115 | Kings | 122 |
| Post | 11, 2000 | Blazers | 123 | Kings | 125 |
| Post | 12, 2000 | Kings | 124 | Blazers | 141 |
| Post | 13, 2000 | Blazers | 130 | Kings | 128 |
| Post | 14, 2000 | Kings | 117 | Blazers | 115 |