| 13 Sep 99 | r01        | Cleveland BrownsCleveland Bro | 43 - 0 | Pittsburgh SteelersPittsburgh St |
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| 19 Sep 99 | r02        | Tennessee TitansTennessee Tit | 26 - 9 | Cleveland BrownsCleveland Bro |
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| 26 Sep 99 | r03        | Baltimore RavensBaltimore Rav | 17 - 10 | Cleveland BrownsCleveland Bro |
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| 03 Oct 99 | r04        | Cleveland BrownsCleveland Bro | 19 - 7 | New England PatriotsNew England P |
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| 10 Oct 99 | r05        | Cleveland BrownsCleveland Bro | 18 - 17 | Cincinnati BengalsCincinnati Be |
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| 17 Oct 99 | r06        | Jacksonville JaguarsJacksonville | 24 - 7 | Cleveland BrownsCleveland Bro |
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| 24 Oct 99 | r07        | Los Angeles RamsLos Angeles R | 34 - 3 | Cleveland BrownsCleveland Bro |
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| 31 Oct 99 | r08        | New Orleans SaintsNew Orleans S | 21 - 16 | Cleveland BrownsCleveland Bro |
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| 07 Nov 99 | r09        | Cleveland BrownsCleveland Bro | 41 - 9 | Baltimore RavensBaltimore Rav |
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| 14 Nov 99 | r10        | Pittsburgh SteelersPittsburgh St | 16 - 15 | Cleveland BrownsCleveland Bro |
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| 21 Nov 99 | r11        | Cleveland BrownsCleveland Bro | 31 - 17 | Carolina PanthersCarolina Pant |
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| 28 Nov 99 | r12        | Cleveland BrownsCleveland Bro | 33 - 21 | Tennessee TitansTennessee Tit |
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| 05 Dec 99 | r13        | Los Angeles ChargersLos Angeles C | 23 - 10 | Cleveland BrownsCleveland Bro |
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| 12 Dec 99 | r14        | Cincinnati BengalsCincinnati Be | 44 - 28 | Cleveland BrownsCleveland Bro |
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| 19 Dec 99 | r15        | Cleveland BrownsCleveland Bro | 24 - 14 | Jacksonville JaguarsJacksonville |
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| 26 Dec 99 | r16        | Cleveland BrownsCleveland Bro | 29 - 28 | Indianapolis ColtsIndianapolis |