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1999 Division I
Class 3A Football Playoff Bracket
| 1st
Round Seeding |
1st Round Nov. 5 |
2nd Round Nov. 12 |
Quarterfinals Nov. 19 |
Semifinals Nov. 26 |
Finals Dec. 3-4 |
State Champions |
| 1st Region 1 | Gatlinburg-Pittman (8-2) 14 |
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| 101 | | Carter 14 | |||||
| 4th Region 2 | Carter (3-7) 24| |
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| 201 | | Sullivan North 12 | |||||
| 2nd Region 2 | Scott County (8-2) 10 |
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| 102 | | Sullivan North 42| | | | ||||
| 3rd Region 1 | Sullivan North (7-3) 14| | | | ||||
| 301 | | Seymour 0 | |||||
| 2nd Region 1 | Seymour (9-1) 21 |
| | | | |||
| 103 | | Seymour 29 | | | | | |||
| 3rd Region 2 | Fulton (7-3) 13| | | | | | | | ||
| 202 | | Seymour 29| | | | ||||
| 4th Region 1 | Rutledge (5-5) 12 | | | | | |||
| 104 | | Kingston 10| | | | ||||
| 1st Region 2 | Kingston (8-2) 42| | | | ||||
| 401 | | Portland 14 | |||||
| 1st Region 3 | Sequoyah (9-1) 14 | | | | | |||
| 105 | | Sequoyah 28 | | | | | |||
| 4th Region 4 | Greenbrier (6-4) 7| |
| | | | | | ||
| 203 | | Sequoyah 28 | | | | | |||
| 2nd Region 4 | White House (8-2) 35 |
| | | | | | | | |
| 106 | | White House 21 | | | | | | | | ||
| 3rd Region 3 | McMinn Central (3-7) 10| |
| | | | | | ||
| 302 | | Portland 21| | | | ||||
| 2nd Region 3 | Brainerd (5-4) 36 | | | | | |||
| 107 | | Brainerd 20 | | | | | |||
| 3rd Region 4 | Livingston Aca. (8-2) 35| |
| | | | | | ||
| 204 | | Portland 46| | | | ||||
| 4th Region 3 | Grundy County (5-5) 7 |
| | | | |||
| 108 | | Portland 34| | | | ||||
| 1st Region 4 | Portland (10-0) 51| | | | ||||
| 501 | | Milan | | |||||
| 1st Region 5 | Page (10-0) 10 | | | ||||
| 109 | | Page 0 | | | ||||
| 4th Region 6 | Bolivar (5-5) 7| |
| | | | |||
| 205 | | J. South Side 8 | | | ||||
| 2nd Region 6 | J. South Side (7-3) 35 | | | | | | | ||
| 110 | | J. South Side 25| | | | | | |||
| 3rd Region 5 | Giles County (6-4) 6| |
| | | | |||
| 303 | | Milan 28 | | | ||||
| 2nd Region 5 | Marshall County (6-4) 14 |
| | | | | | ||
| 111 | | Crockett Co. 0 | | | | | | | ||
| 3rd Region 6 | Crockett Co. (6-4) 30| |
| | | | | | | | |
| 206 | | Milan 29| | | | | | |||
| 4th Region 5 | Montgomery Central (5-5) 8 |
| | | | | | ||
| 112 | | Milan 45| | | | | | |||
| 1st Region 6 | Milan (10-0) 59| | | | | | |||
| 402 | | Milan 21| | |||||
| 1st Region 7 | Covington (9-1) 47 | | | ||||
| 113 | | Covington 9 | | | ||||
| 4th Region 8 | Sheffield (2-6) 0| |
| | | | |||
| 207 | | Covington 34 | | | ||||
| 2nd Region 8 | Westwood (4-5) 34 |
| | | | | | ||
| 114 | | Westwood 0| | | | | | |||
| 3rd Region 7 | Brighton (8-2) 12| |
| | | | |||
| 304 | | Covington 6 | | |||||
| 2nd Region 7 | Westview (8-2) 48 |
| | ||||
| 115 | | Westview 33 | | | ||||
| 3rd Region 8 | Frayser (3-6) 0| |
| | | | |||
| 208 | | Ridgeway 0| | |||||
| 4th Region 7 | Obion Co. (6-4) 9 | | | ||||
| 116 | | Ridgeway 56 | |||||
| 1st Region 8 | Ridgeway (9-1) 46| |
In all play-off games, in the first and second round the higher seeded team shall be the host school. In the third round and semi-finals in odd-numbered years the top team in each bracket shall be the host team. In even numbered years the procedure shall be rotated in the third round and semi-finals. If two teams from the same region play each other in any round, the higher seeded team shall be the host.