| 01 Nov 99 | r01        | New York KnicksNew York Knic | 92 - 84 | Cleveland CavaliersCleveland Cav |
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| 02 Nov 99 | r02        | Cleveland CavaliersCleveland Cav | 97 - 90 | Brooklyn NetsBrooklyn Nets |
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| 04 Nov 99 | r03        | Orlando MagicOrlando Magic | 99 - 104 | Cleveland CavaliersCleveland Cav |
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| 05 Nov 99 | r04        | Cleveland CavaliersCleveland Cav | 102 - 93 | New York KnicksNew York Knic |
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| 10 Nov 99 | r05        | Cleveland CavaliersCleveland Cav | 103 - 109 | Oklahoma City ThunderOklahoma City |
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| 12 Nov 99 | r06        | Cleveland CavaliersCleveland Cav | 117 - 112 | Milwaukee BucksMilwaukee Buc |
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| 16 Nov 99 | r08        | Boston CelticsBoston Celtic | 114 - 103 | Cleveland CavaliersCleveland Cav |
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| 18 Nov 99 | r10        | Detroit PistonsDetroit Pisto | 101 - 90 | Cleveland CavaliersCleveland Cav |
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| 19 Nov 99 | r09        | Cleveland CavaliersCleveland Cav | 98 - 107 | Indiana PacersIndiana Pacer |
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| 22 Nov 99 | r10        | Cleveland CavaliersCleveland Cav | 103 - 100 | Portland Trail BlazersPortland Trai |
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| 25 Nov 99 | r14        | Philadelphia 76ersPhiladelphia | 106 - 83 | Cleveland CavaliersCleveland Cav |
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| 26 Nov 99 | r12        | Cleveland CavaliersCleveland Cav | 106 - 89 | New Orleans PelicansNew Orleans P |
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| 29 Nov 99 | r13        | Cleveland CavaliersCleveland Cav | 106 - 99 | Dallas MavericksDallas Maveri |
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| 30 Nov 99 | r01        | Washington WizardsWashington Wi | 108 - 111 | Cleveland CavaliersCleveland Cav |
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| 02 Dec 99 | r02        | Cleveland CavaliersCleveland Cav | 100 - 102 | Philadelphia 76ersPhiladelphia |
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| 06 Dec 99 | r03        | Toronto RaptorsToronto Rapto | 101 - 98 | Cleveland CavaliersCleveland Cav |
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| 07 Dec 99 | r04        | Cleveland CavaliersCleveland Cav | 107 - 93 | Chicago BullsChicago Bulls |
| 09 Dec 99 | r04        | Indiana PacersIndiana Pacer | 136 - 88 | Cleveland CavaliersCleveland Cav |
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| 10 Dec 99 | r06        | Cleveland CavaliersCleveland Cav | 127 - 116 | Atlanta HawksAtlanta Hawks |
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| 13 Dec 99 | r07        | Cleveland CavaliersCleveland Cav | 115 - 88 | Boston CelticsBoston Celtic |
| 14 Dec 99 | r07        | Brooklyn NetsBrooklyn Nets | 111 - 101 | Cleveland CavaliersCleveland Cav |
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| 16 Dec 99 | r08        | New Orleans PelicansNew Orleans P | 99 - 86 | Cleveland CavaliersCleveland Cav |
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| 17 Dec 99 | r10        | Cleveland CavaliersCleveland Cav | 74 - 98 | Brooklyn NetsBrooklyn Nets |
| 19 Dec 99 | r10        | Cleveland CavaliersCleveland Cav | 94 - 100 | Minnesota TimberwolvesMinnesota Tim |
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| 21 Dec 99 | r12        | Cleveland CavaliersCleveland Cav | 97 - 103 | Orlando MagicOrlando Magic |
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| 22 Dec 99 | r10        | Atlanta HawksAtlanta Hawks | 108 - 90 | Cleveland CavaliersCleveland Cav |
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| 25 Dec 99 | r14        | Cleveland CavaliersCleveland Cav | 95 - 98 | Toronto RaptorsToronto Rapto |
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| 28 Dec 99 | r15        | Cleveland CavaliersCleveland Cav | 96 - 94 | Washington WizardsWashington Wi |
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| 29 Dec 99 | r16        | Milwaukee BucksMilwaukee Buc | 91 - 90 | Cleveland CavaliersCleveland Cav |
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| 02 Jan 00 | r01        | Boston CelticsBoston Celtic | 105 - 98 | Cleveland CavaliersCleveland Cav |
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| 03 Jan 00 | r02        | Cleveland CavaliersCleveland Cav | 107 - 111 | Sacramento KingsSacramento Ki |
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| 05 Jan 00 | r03        | Cleveland CavaliersCleveland Cav | 90 - 75 | Golden State WarriorsGolden State |
| 07 Jan 00 | r03        | New York KnicksNew York Knic | 86 - 89 | Cleveland CavaliersCleveland Cav |
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| 09 Jan 00 | r05        | Cleveland CavaliersCleveland Cav | 111 - 106 | Los Angeles ClippersLos Angeles C |
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| 11 Jan 00 | r06        | Portland Trail BlazersPortland Trai | 95 - 75 | Cleveland CavaliersCleveland Cav |
| 13 Jan 00 | r06        | Memphis GrizzliesMemphis Grizz | 80 - 82 | Cleveland CavaliersCleveland Cav |
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| 15 Jan 00 | r08        | Sacramento KingsSacramento Ki | 113 - 102 | Cleveland CavaliersCleveland Cav |
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| 17 Jan 00 | r09        | Oklahoma City ThunderOklahoma City | 99 - 80 | Cleveland CavaliersCleveland Cav |
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| 18 Jan 00 | r10        | Los Angeles LakersLos Angeles L | 95 - 86 | Cleveland CavaliersCleveland Cav |
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| 20 Jan 00 | r09        | Golden State WarriorsGolden State | 115 - 103 | Cleveland CavaliersCleveland Cav |
| 21 Jan 00 | r09        | Phoenix SunsPhoenix Suns | 101 - 88 | Cleveland CavaliersCleveland Cav |
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| 24 Jan 00 | r13        | Cleveland CavaliersCleveland Cav | 116 - 107 | Detroit PistonsDetroit Pisto |
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| 26 Jan 00 | r14        | Cleveland CavaliersCleveland Cav | 102 - 90 | Orlando MagicOrlando Magic |
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| 28 Jan 00 | r15        | Washington WizardsWashington Wi | 103 - 98 | Cleveland CavaliersCleveland Cav |
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| 31 Jan 00 | r01        | Cleveland CavaliersCleveland Cav | 112 - 108 | Washington WizardsWashington Wi |
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| 03 Feb 00 | r02        | Detroit PistonsDetroit Pisto | 105 - 96 | Cleveland CavaliersCleveland Cav |
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| 04 Feb 00 | r03        | Cleveland CavaliersCleveland Cav | 94 - 102 | Atlanta HawksAtlanta Hawks |
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| 07 Feb 00 | r05        | Houston RocketsHouston Rocke | 91 - 83 | Cleveland CavaliersCleveland Cav |
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| 08 Feb 00 | r04        | New Orleans PelicansNew Orleans P | 103 - 95 | Cleveland CavaliersCleveland Cav |
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| 14 Feb 00 | r06        | Cleveland CavaliersCleveland Cav | 92 - 81 | San Antonio SpursSan Antonio S |
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| 16 Feb 00 | r07        | Cleveland CavaliersCleveland Cav | 119 - 101 | Denver NuggetsDenver Nugget |
| 17 Feb 00 | r07        | Philadelphia 76ersPhiladelphia | 104 - 75 | Cleveland CavaliersCleveland Cav |
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| 20 Feb 00 | r09        | Cleveland CavaliersCleveland Cav | 109 - 108 | Memphis GrizzliesMemphis Grizz |
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| 22 Feb 00 | r10        | Cleveland CavaliersCleveland Cav | 98 - 116 | Los Angeles LakersLos Angeles L |
| 24 Feb 00 | r10        | Miami HeatMiami Heat | 87 - 82 | Cleveland CavaliersCleveland Cav |
| 28 Feb 00 | r10        | Cleveland CavaliersCleveland Cav | 93 - 100 | Phoenix SunsPhoenix Suns |
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| 01 Mar 00 | r01        | Chicago BullsChicago Bulls | 110 - 114 | Cleveland CavaliersCleveland Cav |
| 03 Mar 00 | r01        | Los Angeles ClippersLos Angeles C | 99 - 109 | Cleveland CavaliersCleveland Cav |
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| 04 Mar 00 | r03        | Denver NuggetsDenver Nugget | 92 - 100 | Cleveland CavaliersCleveland Cav |
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| 06 Mar 00 | r04        | Utah JazzUtah Jazz | 113 - 95 | Cleveland CavaliersCleveland Cav |
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| 09 Mar 00 | r05        | Cleveland CavaliersCleveland Cav | 92 - 95 | Indiana PacersIndiana Pacer |
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| 11 Mar 00 | r06        | Milwaukee BucksMilwaukee Buc | 103 - 72 | Cleveland CavaliersCleveland Cav |
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| 13 Mar 00 | r07        | Cleveland CavaliersCleveland Cav | 97 - 98 | Philadelphia 76ersPhiladelphia |
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| 15 Mar 00 | r08        | Cleveland CavaliersCleveland Cav | 86 - 107 | Utah JazzUtah Jazz |
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| 17 Mar 00 | r09        | Cleveland CavaliersCleveland Cav | 90 - 92 | Miami HeatMiami Heat |
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| 19 Mar 00 | r10        | Cleveland CavaliersCleveland Cav | 98 - 85 | Houston RocketsHouston Rocke |
| 20 Mar 00 | r10        | Minnesota TimberwolvesMinnesota Tim | 111 - 107 | Cleveland CavaliersCleveland Cav |
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| 22 Mar 00 | r12        | Dallas MavericksDallas Maveri | 98 - 104 | Cleveland CavaliersCleveland Cav |
| 24 Mar 00 | r12        | San Antonio SpursSan Antonio S | 96 - 76 | Cleveland CavaliersCleveland Cav |
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| 27 Mar 00 | r14        | Cleveland CavaliersCleveland Cav | 96 - 99 | Toronto RaptorsToronto Rapto |
| 28 Mar 00 | r14        | Chicago BullsChicago Bulls | 81 - 86 | Cleveland CavaliersCleveland Cav |
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| 31 Mar 00 | r01        | Cleveland CavaliersCleveland Cav | 109 - 103 | Boston CelticsBoston Celtic |
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| 01 Apr 00 | r02        | Cleveland CavaliersCleveland Cav | 74 - 83 | Chicago BullsChicago Bulls |
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| 03 Apr 00 | r07        | Miami HeatMiami Heat | 111 - 85 | Cleveland CavaliersCleveland Cav |
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| 06 Apr 00 | r03        | Indiana PacersIndiana Pacer | 95 - 94 | Cleveland CavaliersCleveland Cav |
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| 07 Apr 00 | r04        | Cleveland CavaliersCleveland Cav | 117 - 98 | Detroit PistonsDetroit Pisto |
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| 09 Apr 00 | r05        | Toronto RaptorsToronto Rapto | 112 - 103 | Cleveland CavaliersCleveland Cav |
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| 11 Apr 00 | r06        | Cleveland CavaliersCleveland Cav | 100 - 101 | Milwaukee BucksMilwaukee Buc |
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| 14 Apr 00 | r07        | Cleveland CavaliersCleveland Cav | 106 - 96 | New York KnicksNew York Knic |
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| 15 Apr 00 | r09        | Atlanta HawksAtlanta Hawks | 104 - 101 | Cleveland CavaliersCleveland Cav |
| 17 Apr 00 | r09        | Cleveland CavaliersCleveland Cav | 88 - 103 | New Orleans PelicansNew Orleans P |
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| 18 Apr 00 | r10        | Brooklyn NetsBrooklyn Nets | 108 - 111 | Cleveland CavaliersCleveland Cav |