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| Aug. 27, 1999 Weekend |
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| Detroit Chadsey 20, Detroit Northwestern 0 |
* |
|
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| Detroit Martin Luther King 10, Detroit Redford 8 |
* |
|
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| Detroit Murray-Wright 28, Detroit Mackenzie 0 |
* |
|
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| Detroit Pershing 18, Detroit Cody 15 |
* |
|
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| Westland Glenn 17, Detroit Cooley 6 |
* |
|
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| |
| Sep. 3, 1999 Weekend |
|
| Detroit Cody 15, Detroit Cooley 12 |
|
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|
| Detroit Henry Ford 45, Detroit Redford 0 |
|
|
|
| Detroit Mackenzie 26, Detroit Northwestern 14 |
|
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|
| |
| Sep. 10, 1999 Weekend |
|
| Detroit Cody 30, Detroit Northwestern 0 |
|
|
|
| Detroit Henry Ford 41, Detroit Cooley 8 |
|
|
|
| Detroit Redford 33, Detroit Mackenzie 12 |
|
|
|
| |
| Sep. 17, 1999 Weekend |
|
| Detroit Cooley 10, Detroit Northwestern 0 |
|
|
|
| Detroit Henry Ford 37, Detroit Mackenzie 6 |
|
|
|
| Detroit Redford 13, Detroit Cody 0 |
|
|
|
| |
| Sep. 24, 1999 Weekend |
|
| Detroit Cooley 30, Detroit Mackenzie 22 |
|
|
|
| Detroit Henry Ford 48, Detroit Cody 0 |
|
|
|
| Detroit Redford 20, Detroit Northwestern 0 |
|
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|
| |
| Oct. 1, 1999 Weekend |
|
| Detroit Cody 28, Detroit Mackenzie 12 |
|
|
|
| Detroit Cooley 8, Detroit Redford 0 |
|
|
|
| Detroit Henry Ford 55, Detroit Northwestern 0 |
|
|
|
| |
| Oct. 8, 1999 Weekend |
|
| Detroit Cooley 12, Detroit Crockett 6 |
* |
|
|
| Detroit Henry Ford 31, Detroit Central 6 |
* |
|
|
| Detroit Mackenzie 17, Detroit Western 14 |
* |
|
|
| Detroit Northwestern 6, Detroit Southeastern 0 |
* |
|
|
| Detroit Redford 18, Detroit Southwestern 8 |
* |
|
|
| Detroit Renaissance 16, Detroit Cody 6 |
* |
|
|
| |
| Oct. 15, 1999 Weekend |
|
| Detroit Chadsey 26, Detroit Cody 18 |
* |
|
|
| Detroit Cooley 8, Detroit Pershing 6 |
* |
|
|
| Detroit Denby 24, Detroit Redford 14 |
* |
|
|
| Detroit Henry Ford 23, Detroit Martin Luther King 6 |
* |
|
|
| Detroit Mumford 14, Detroit Mackenzie 13 |
* |
|
|
| Detroit Osborn 20, Detroit Northwestern 2 |
* |
|
|
| |
| Oct. 22, 1999 Weekend |
|
| Detroit Cooley 12, Detroit Mumford 0 |
* |
|
|
| Detroit Denby 34, Detroit Mackenzie 0 |
* |
|
|
| Detroit Henry Ford 7, Detroit Cass Tech 6 |
* |
|
|
| Detroit Kettering 22, Detroit Cody 16 |
* |
|
|
| Detroit Redford 28, Detroit Murray-Wright 14 |
* |
|
|
| Detroit Western 36, Detroit Northwestern 26 |
* |
|
|
| |
| Oct. 29, 1999 Weekend |
|
| Detroit Henry Ford 40, Belleville 25 |
* |
|
PRE-DISTRICT |
| Detroit Martin Luther King 35, Detroit Cooley 0 |
* |
|
PRE-DISTRICT |
| |
| Nov. 5, 1999 Weekend |
|
| Westland Glenn 27, Detroit Henry Ford 23 |
* |
|
DISTRICT FINAL |
* indicates that game is non-conference
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