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| Aug. 27, 1999 Weekend |
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| Clinton 26, Manchester 14 |
* |
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| Concord 35, Hanover-Horton 0 |
* |
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| East Jackson 27, Leslie 14 |
* |
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| Grass Lake 69, Waldron 0 |
* |
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| Napoleon 28, Brooklyn Columbia Central 7 |
* |
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| Onsted 20, Addison 7 |
* |
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| Parma Jackson County Western 27, Michigan Center 0 |
* |
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| Springport 8, Jackson Vandercook Lake 7 |
* |
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| Sep. 3, 1999 Weekend |
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| Addison 34, Jackson Vandercook Lake 18 |
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| East Jackson 37, Hanover-Horton 0 |
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| Grass Lake 20, Napoleon 13 |
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| Michigan Center 9, Manchester 7 |
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| Sep. 10, 1999 Weekend |
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| Addison 41, Michigan Center 0 |
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| East Jackson 32, Napoleon 8 |
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| Grass Lake 62, Jackson Vandercook Lake 8 |
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| Manchester 17, Hanover-Horton 14 |
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| Sep. 17, 1999 Weekend |
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| Addison 21, Napoleon 18 |
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| East Jackson 56, Jackson Vandercook Lake 0 |
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| Grass Lake 27, Manchester 0 |
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| Hanover-Horton 44, Michigan Center 28 |
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| Sep. 24, 1999 Weekend |
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| East Jackson 27, Michigan Center 14 |
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| Grass Lake 41, Hanover-Horton 6 |
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| Jackson Vandercook Lake 13, Napoleon 6 |
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| Manchester 14, Addison 13 |
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| Oct. 1, 1999 Weekend |
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| Addison 14, Hanover-Horton 7 |
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| Grass Lake 7, East Jackson 3 |
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| Jackson Vandercook Lake 18, Michigan Center 13 |
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| Manchester 28, Napoleon 7 |
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| Oct. 8, 1999 Weekend |
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| Addison 27, East Jackson 6 |
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| Grass Lake 47, Michigan Center 0 |
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| Manchester 24, Jackson Vandercook Lake 0 |
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| Napoleon 28, Hanover-Horton 26 |
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| Oct. 15, 1999 Weekend |
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| Addison 14, Grass Lake 0 |
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| East Jackson 27, Manchester 0 |
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| Jackson Vandercook Lake 21, Hanover-Horton 14 |
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| Napoleon 39, Michigan Center 8 |
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| Oct. 22, 1999 Weekend |
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| Concord 47, Jackson Vandercook Lake 24 |
* |
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| East Jackson 26, Athens 14 |
* |
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| Grass Lake 21, Reading 12 |
* |
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| Jonesville 28, Hanover-Horton 12 |
* |
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| Manchester 7, Union City 0 |
* |
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| Napoleon 28, Homer 8 |
* |
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| Quincy 20, Addison 7 |
* |
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| Springport 13, Michigan Center 3 |
* |
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| |
| Oct. 29, 1999 Weekend |
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| Addison 16, Quincy 12 |
* |
|
PRE-DISTRICT |
| Albion 34, East Jackson 7 |
* |
|
PRE-DISTRICT |
| Grass Lake 35, Manchester 0 |
* |
|
PRE-DISTRICT |
| |
| Nov. 5, 1999 Weekend |
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| Addison 28, Albion 14 |
* |
|
DISTRICT FINAL |
| Sand Creek 20, Grass Lake 19 |
* |
|
DISTRICT FINAL |
| |
| Nov. 12, 1999 Weekend |
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| Addison 35, Clinton 17 |
* |
|
REGIONAL FINAL |
| |
| Nov. 19, 1999 Weekend |
|
| Hopkins 34, Addison 0 |
* |
|
STATE SEMIFINAL |
* indicates that game is non-conference
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