| Cavaliers Games/Schedule |
| Oct. 28, 2008 | Round 1 (Regular Season ) | Cavaliers-Celtics | 85-90 |
| Oct. 30, 2008 | Round 3 (Regular Season ) | Bobcats-Cavaliers | 79-96 |
| Nov. 1, 2008 | Round 5 (Regular Season ) | Cavaliers-Hornets | 92-104 |
| Nov. 3, 2008 | Round 7 (Regular Season ) | Cavaliers-Mavericks | 100-81 |
| Nov. 5, 2008 | Round 9 (Regular Season ) | Bulls-Cavaliers | 93-107 |
| Nov. 7, 2008 | Round 11 (Regular Season ) | Pacers-Cavaliers | 107-111 |
| Nov. 8, 2008 | Round 12 (Regular Season ) | Cavaliers-Bulls | 106-97 |
| Nov. 11, 2008 | Round 15 (Regular Season ) | Bucks-Cavaliers | 93-99 |
| Nov. 13, 2008 | Round 17 (Regular Season ) | Nuggets-Cavaliers | 99-110 |
| Nov. 15, 2008 | Round 19 (Regular Season ) | Jazz-Cavaliers | 93-105 |
| Nov. 18, 2008 | Round 22 (Regular Season ) | Cavaliers-Nets | 106-82 |
| Nov. 19, 2008 | Round 23 (Regular Season ) | Cavaliers-Pistons | 89-96 |
| Nov. 22, 2008 | Round 26 (Regular Season ) | Hawks-Cavaliers | 96-110 |
| Nov. 25, 2008 | Round 29 (Regular Season ) | Cavaliers-Knicks | 119-101 |
| Nov. 26, 2008 | Round 30 (Regular Season ) | Thunder-Cavaliers | 82-117 |
| Nov. 28, 2008 | Round 32 (Regular Season ) | Warriors-Cavaliers | 97-112 |
| Nov. 29, 2008 | Round 33 (Regular Season ) | Cavaliers-Bucks | 97-85 |
| Dec. 3, 2008 | Round 37 (Regular Season ) | Knicks-Cavaliers | 82-118 |
| Dec. 5, 2008 | Round 39 (Regular Season ) | Pacers-Cavaliers | 73-97 |
| Dec. 6, 2008 | Round 40 (Regular Season ) | Cavaliers-Bobcats | 94-74 |
| Dec. 9, 2008 | Round 43 (Regular Season ) | Raptors-Cavaliers | 94-114 |
| Dec. 10, 2008 | Round 44 (Regular Season ) | Cavaliers-76ers | 101-93 |
| Dec. 12, 2008 | Round 46 (Regular Season ) | 76ers-Cavaliers | 72-88 |
| Dec. 13, 2008 | Round 47 (Regular Season ) | Cavaliers-Hawks | 92-97 |
| Dec. 17, 2008 | Round 51 (Regular Season ) | Cavaliers-Timberwolves | 93-70 |
| Dec. 19, 2008 | Round 53 (Regular Season ) | Cavaliers-Nuggets | 105-88 |
| Dec. 21, 2008 | Round 55 (Regular Season ) | Cavaliers-Thunder | 102-91 |
| Dec. 23, 2008 | Round 57 (Regular Season ) | Rockets-Cavaliers | 90-99 |
| Dec. 25, 2008 | Round 58 (Regular Season ) | Wizards-Cavaliers | 89-93 |
| Dec. 28, 2008 | Round 61 (Regular Season ) | Heat-Cavaliers | 86-93 |
| Dec. 30, 2008 | Round 63 (Regular Season ) | Cavaliers-Heat | 95-104 |
| Jan. 2, 2009 | Round 65 (Regular Season ) | Bulls-Cavaliers | 92-117 |
| Jan. 4, 2009 | Round 67 (Regular Season ) | Cavaliers-Wizards | 77-80 |
| Jan. 7, 2009 | Round 70 (Regular Season ) | Bobcats-Cavaliers | 81-101 |
| Jan. 9, 2009 | Round 72 (Regular Season ) | Celtics-Cavaliers | 83-98 |
| Jan. 13, 2009 | Round 76 (Regular Season ) | Cavaliers-Grizzlies | 102-87 |
| Jan. 15, 2009 | Round 78 (Regular Season ) | Cavaliers-Bulls | 93-102 |
| Jan. 16, 2009 | Round 79 (Regular Season ) | Hornets-Cavaliers | 78-92 |
| Jan. 19, 2009 | Round 82 (Regular Season ) | Cavaliers-Lakers | 88-105 |
| Jan. 21, 2009 | Round 84 (Regular Season ) | Cavaliers-Trail Blazers | 104-98 |
| Jan. 23, 2009 | Round 86 (Regular Season ) | Cavaliers-Warriors | 106-105 |
| Jan. 24, 2009 | Round 87 (Regular Season ) | Cavaliers-Jazz | 102-97 |
| Jan. 27, 2009 | Round 90 (Regular Season ) | Kings-Cavaliers | 110-117 |
| Jan. 29, 2009 | Round 92 (Regular Season ) | Cavaliers-Magic | 88-99 |
| Jan. 30, 2009 | Round 93 (Regular Season ) | Clippers-Cavaliers | 95-112 |
| Feb. 1, 2009 | Round 95 (Regular Season ) | Cavaliers-Pistons | 90-80 |
| Feb. 3, 2009 | Round 97 (Regular Season ) | Raptors-Cavaliers | 83-101 |
| Feb. 4, 2009 | Round 98 (Regular Season ) | Cavaliers-Knicks | 107-102 |
| Feb. 8, 2009 | Round 102 (Regular Season ) | Lakers-Cavaliers | 101-91 |
| Feb. 10, 2009 | Round 104 (Regular Season ) | Cavaliers-Pacers | 95-96 |
| Feb. 11, 2009 | Round 105 (Regular Season ) | Suns-Cavaliers | 92-109 |
| Feb. 18, 2009 | Round 108 (Regular Season ) | Cavaliers-Raptors | 93-76 |
| Feb. 20, 2009 | Round 110 (Regular Season ) | Cavaliers-Bucks | 111-103 |
| Feb. 22, 2009 | Round 112 (Regular Season ) | Pistons-Cavaliers | 78-99 |
| Feb. 24, 2009 | Round 114 (Regular Season ) | Grizzlies-Cavaliers | 79-94 |
| Feb. 26, 2009 | Round 116 (Regular Season ) | Cavaliers-Rockets | 74-93 |
| Feb. 27, 2009 | Round 117 (Regular Season ) | Cavaliers-Spurs | 97-86 |
| Mar. 1, 2009 | Round 119 (Regular Season ) | Cavaliers-Hawks | 88-87 |
| Mar. 2, 2009 | Round 120 (Regular Season ) | Cavaliers-Heat | 107-100 |
| Mar. 4, 2009 | Round 122 (Regular Season ) | Bucks-Cavaliers | 73-91 |
| Mar. 6, 2009 | Round 124 (Regular Season ) | Cavaliers-Celtics | 94-105 |
| Mar. 7, 2009 | Round 125 (Regular Season ) | Heat-Cavaliers | 89-99 |
| Mar. 10, 2009 | Round 128 (Regular Season ) | Cavaliers-Clippers | 87-83 |
| Mar. 12, 2009 | Round 130 (Regular Season ) | Cavaliers-Suns | 119-111 |
| Mar. 13, 2009 | Round 131 (Regular Season ) | Cavaliers-Kings | 126-123 |
| Mar. 15, 2009 | Round 133 (Regular Season ) | Knicks-Cavaliers | 93-98 |
| Mar. 17, 2009 | Round 135 (Regular Season ) | Magic-Cavaliers | 93-97 |
| Mar. 19, 2009 | Round 137 (Regular Season ) | Trail Blazers-Cavaliers | 92-97 |
| Mar. 21, 2009 | Round 139 (Regular Season ) | Hawks-Cavaliers | 96-102 |
| Mar. 22, 2009 | Round 140 (Regular Season ) | Cavaliers-Nets | 96-88 |
| Mar. 25, 2009 | Round 143 (Regular Season ) | Nets-Cavaliers | 87-98 |
| Mar. 27, 2009 | Round 145 (Regular Season ) | Timberwolves-Cavaliers | 85-107 |
| Mar. 29, 2009 | Round 147 (Regular Season ) | Mavericks-Cavaliers | 74-102 |
| Mar. 31, 2009 | Round 149 (Regular Season ) | Pistons-Cavaliers | 73-79 |
| Apr. 2, 2009 | Round 151 (Regular Season ) | Cavaliers-Wizards | 101-109 |
| Apr. 3, 2009 | Round 152 (Regular Season ) | Cavaliers-Magic | 87-116 |
| Apr. 5, 2009 | Round 154 (Regular Season ) | Spurs-Cavaliers | 81-101 |
| Apr. 8, 2009 | Round 156 (Regular Season ) | Wizards-Cavaliers | 86-98 |
| Apr. 10, 2009 | Round 158 (Regular Season ) | Cavaliers-76ers | 102-92 |
| Apr. 12, 2009 | Round 160 (Regular Season ) | Celtics-Cavaliers | 76-107 |
| Apr. 13, 2009 | Round 161 (Regular Season ) | Cavaliers-Pacers | 117-109 |
| Apr. 15, 2009 | Round 163 (Regular Season ) | 76ers-Cavaliers | 111-110 |
| Apr. 18, 2009 | Round 1 (1/8 Finals ) | Pistons-Cavaliers | 84-102 |
| Apr. 21, 2009 | Round 2 (1/8 Finals ) | Pistons-Cavaliers | 82-94 |
| Apr. 24, 2009 | Round 3 (1/8 Finals ) | Cavaliers-Pistons | 79-68 |
| Apr. 26, 2009 | Round 4 (1/8 Finals ) | Cavaliers-Pistons | 99-78 |
| May. 5, 2009 | Round 1 (Quarter-Finals ) | Hawks-Cavaliers | 72-99 |
| May. 7, 2009 | Round 2 (Quarter-Finals ) | Hawks-Cavaliers | 85-105 |
| May. 9, 2009 | Round 3 (Quarter-Finals ) | Cavaliers-Hawks | 97-82 |
| May. 11, 2009 | Round 4 (Quarter-Finals ) | Cavaliers-Hawks | 84-74 |
| May. 20, 2009 | Round 1 (Semi-Finals ) | Magic-Cavaliers | 107-106 |
| May. 22, 2009 | Round 2 (Semi-Finals ) | Magic-Cavaliers | 95-96 |
| May. 24, 2009 | Round 3 (Semi-Finals ) | Cavaliers-Magic | 89-99 |
| May. 26, 2009 | Round 4 (Semi-Finals ) | Cavaliers-Magic | 114-116 |
| May. 28, 2009 | Round 5 (Semi-Finals ) | Magic-Cavaliers | 102-112 |
| May. 30, 2009 | Round 6 (Semi-Finals ) | Cavaliers-Magic | 90-103 |
