1999-00 Cleveland Cavaliers (32-50)

2 Nov L at New York 84- 92  
(0-1)
3 Nov W New Jersey 97- 90  
(1-1)
5 Nov W at Orlando 104- 99  
(2-1)
6 Nov W New York 102- 93  
(3-1)
11 Nov L Seattle 103- 109  
(3-2)
13 Nov W Milwaukee 117- 112  
(4-2)
17 Nov L at Boston 103- 114  
(4-3)
19 Nov L at Detroit 90- 101  
(4-4)
20 Nov L Indiana 98- 107  
(4-5)
23 Nov W Portland 103- 100  
(5-5)
26 Nov L at Philadelphia 83- 106  
(5-6)
27 Nov W Charlotte 106- 89  
(6-6)
30 Nov W Dallas 106- 99  
(7-6)
1 Dec W at Washington 111- 108  
(8-6)
3 Dec L Philadelphia 100- 102 (O)
(8-7)
7 Dec L at Toronto 98- 101  
(8-8)
8 Dec W Chicago 107- 93  
(9-8)
10 Dec L at Indiana 88- 136  
(9-9)
11 Dec W Atlanta 127- 116  
(10-9)
14 Dec W Boston 115- 88  
(11-9)
15 Dec L at New Jersey 101- 111  
(11-10)
17 Dec L at Charlotte 86- 99  
(11-11)
18 Dec L New Jersey 74- 98  
(11-12)
20 Dec L Minnesota 94- 100  
(11-13)
22 Dec L Orlando 97- 103  
(11-14)
23 Dec L at Atlanta 90- 108  
(11-15)
26 Dec L Toronto 95- 98  
(11-16)
29 Dec W Washington 96- 94  
(12-16)
30 Dec L at Milwaukee 90- 91  
(12-17)
3 Jan L at Boston 98- 105  
(12-18)
4 Jan L Sacramento 107- 111  
(12-19)
6 Jan W Golden State 90- 75  
(13-19)
8 Jan W at New York 89- 86  
(14-19)
10 Jan W LA Clippers 111- 106  
(15-19)
12 Jan L at Portland 75- 95  
(15-20)
14 Jan W at Vancouver 82- 80  
(16-20)
16 Jan L at Sacramento 102- 113  
(16-21)
18 Jan L at Seattle 80- 99  
(16-22)
19 Jan L at LA Lakers 86- 95  
(16-23)
21 Jan L at Golden State 103- 115  
(16-24)
22 Jan L at Phoenix 88- 101  
(16-25)
25 Jan W Detroit 116- 107 (O)
(17-25)
27 Jan W Orlando 102- 90  
(18-25)
29 Jan L at Washington 98- 103  
(18-26)
1 Feb W Washington 112- 108  
(19-26)
4 Feb L at Detroit 96- 105  
(19-27)
5 Feb L Atlanta 94- 102  
(19-28)
8 Feb L at Houston 83- 91  
(19-29)
9 Feb L at Charlotte 95- 103  
(19-30)
15 Feb W San Antonio 92- 81  
(20-30)
17 Feb W Denver 119- 101  
(21-30)
18 Feb L at Philadelphia 75- 104  
(21-31)
21 Feb W Vancouver 109- 108 (O)
(22-31)
23 Feb L LA Lakers 98- 116  
(22-32)
25 Feb L at Miami 82- 87  
(22-33)
29 Feb L Phoenix 93- 100  
(22-34)
2 Mar W at Chicago 114- 110 (O)
(23-34)
4 Mar W at LA Clippers 109- 99  
(24-34)
5 Mar W at Denver 100- 92  
(25-34)
7 Mar L at Utah 95- 113  
(25-35)
10 Mar L Indiana 92- 95  
(25-36)
12 Mar L at Milwaukee 72- 103  
(25-37)
14 Mar L Philadelphia 97- 98 (O)
(25-38)
16 Mar L Utah 86- 107  
(25-39)
18 Mar L Miami 90- 92 (O)
(25-40)
20 Mar W Houston 98- 85  
(26-40)
21 Mar L at Minnesota 107- 111 (O)
(26-41)
23 Mar W at Dallas 104- 98  
(27-41)
25 Mar L at San Antonio 76- 96  
(27-42)
28 Mar L Toronto 96- 99  
(27-43)
29 Mar W at Chicago 86- 81  
(28-43)
1 Apr W Boston 109- 103  
(29-43)
2 Apr L Chicago 74- 83  
(29-44)
4 Apr L at Miami 85- 111  
(29-45)
7 Apr L at Indiana 94- 95  
(29-46)
8 Apr W Detroit 117- 98  
(30-46)
10 Apr L at Toronto 103- 112  
(30-47)
12 Apr L Milwaukee 100- 101  
(30-48)
15 Apr W New York 106- 96  
(31-48)
16 Apr L at Atlanta 101- 104  
(31-49)
18 Apr L Charlotte 88- 103  
(31-50)
19 Apr W at New Jersey 111- 108  
(32-50)