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| Aug. 27, 1999 Weekend |
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| Bath 25, Dansville 15 |
* |
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| East Jackson 27, Leslie 14 |
* |
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| Laingsburg 14, Webberville 6 |
* |
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| Morrice 31, Marine City Cardinal Mooney 0 |
* |
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| Potterville 36, Bellevue 7 |
* |
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| Vermontville Maple Valley 8, Union City 0 |
* |
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| Williamston 12, Olivet 7 |
* |
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| |
| Sep. 3, 1999 Weekend |
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| Bellevue 34, Webberville 6 |
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| Dansville 48, Whitmore Lake 12 |
* |
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| Olivet 20, Leslie 6 |
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| Vermontville Maple Valley 29, Morrice 6 |
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| Sep. 10, 1999 Weekend |
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| Dansville 52, Webberville 28 |
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| Morenci 14, Leslie 8 |
* |
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| Morrice 28, Bellevue 13 |
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| Vermontville Maple Valley 32, Olivet 17 |
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| |
| Sep. 17, 1999 Weekend |
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| Bellevue 28, Stockbridge 19 |
* |
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| Dansville 21, Morrice 8 |
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| Olivet 57, Webberville 8 |
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| Vermontville Maple Valley 47, Leslie 8 |
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| |
| Sep. 24, 1999 Weekend |
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| Morrice 27, Leslie 22 |
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| Olivet 42, Dansville 6 |
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| Vermontville Maple Valley 24, Bellevue 6 |
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| Whitmore Lake 33, Webberville 30 |
* |
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| |
| Oct. 1, 1999 Weekend |
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| Leslie 20, Dansville 6 |
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| Morrice 50, North Branch Heritage Christian 0 |
* |
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| Olivet 21, Bellevue 0 |
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| Vermontville Maple Valley 55, Webberville 0 |
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| |
| Oct. 8, 1999 Weekend |
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| Bellevue 15, Leslie 14 |
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| Morrice 41, Webberville 12 |
|
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| Olivet 16, Portland 13 |
* |
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| Vermontville Maple Valley 31, Dansville 0 |
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| |
| Oct. 15, 1999 Weekend |
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| Bellevue 18, Dansville 14 |
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| Leslie 54, Webberville 12 |
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| Olivet 51, Morrice 0 |
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| Vermontville Maple Valley 20, Williamston 14 |
* |
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| |
| Oct. 22, 1999 Weekend |
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| Bath 29, Morrice 28 |
* |
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| Bellevue 42, Wyoming Lee 41 |
* |
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| Dansville 17, Saranac 8 |
* |
|
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| Leslie 42, Stockbridge 12 |
* |
|
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| Olivet 28, Eaton Rapids 21 |
* |
|
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| Potterville 47, Webberville 7 |
* |
|
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| Vermontville Maple Valley 36, Portland 28 |
* |
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| |
| Oct. 29, 1999 Weekend |
|
| Morrice 39, Kingston 0 |
* |
|
PRE-DISTRICT |
| Vermontville Maple Valley 22, Olivet 10 |
* |
|
PRE-DISTRICT |
| |
| Nov. 5, 1999 Weekend |
|
| Berrien Springs 10, Vermontville Maple Valley 6 |
* |
|
DISTRICT FINAL |
| Waterford Our Lady of the Lakes 35, Morrice 13 |
* |
|
DISTRICT FINAL |
* indicates that game is non-conference
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