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| Aug. 27, 1999 Weekend |
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| Belleville 32, Fraser 31 |
* |
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| Canton 14, Ypsilanti 8 |
* |
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| Detroit Kettering 23, Dearborn Fordson 6 |
* |
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| Livonia Franklin 28, Lincoln Park 13 |
* |
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| Livonia Stevenson 26, Dearborn 7 |
* |
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| Romulus 21, Wayne Memorial 12 |
* |
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| Saginaw 34, Monroe 6 |
* |
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| Sep. 3, 1999 Weekend |
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| Belleville 13, Dearborn 6 |
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| Dearborn Fordson 13, Wayne Memorial 6 |
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| Monroe 26, Lincoln Park 0 |
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| Ypsilanti 26, Woodhaven 0 |
* |
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| Sep. 10, 1999 Weekend |
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| Belleville 46, Redford Union 18 |
* |
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| Dearborn Fordson 23, Dearborn 7 |
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| Monroe 27, Wayne Memorial 11 |
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| Ypsilanti 27, Lincoln Park 13 |
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| Sep. 17, 1999 Weekend |
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| Belleville 20, Lincoln Park 0 |
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| Dearborn 14, Wayne Memorial 10 |
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| Monroe 20, Allen Park 6 |
* |
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| Ypsilanti 17, Dearborn Fordson 14 |
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| Sep. 24, 1999 Weekend |
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| Belleville 24, Wayne Memorial 6 |
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| Dearborn 28, Dearborn Edsel Ford 3 |
* |
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| Lincoln Park 18, Dearborn Fordson 12 |
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| Monroe 22, Ypsilanti 14 |
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| Oct. 1, 1999 Weekend |
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| Dearborn Fordson 17, Taylor Truman 14 |
* |
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| Lincoln Park 12, Wayne Memorial 0 |
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| Monroe 35, Belleville 14 |
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| Ypsilanti 27, Dearborn 14 |
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| Oct. 8, 1999 Weekend |
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| Lincoln Park 14, Dearborn 0 |
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| Monroe 21, Dearborn Fordson 3 |
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| Wyandotte 34, Wayne Memorial 6 |
* |
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| Ypsilanti 29, Belleville 7 |
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| Oct. 15, 1999 Weekend |
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| Dearborn Fordson 23, Belleville 20 |
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| Garden City 28, Lincoln Park 13 |
* |
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| Monroe 35, Dearborn 20 |
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| Ypsilanti 45, Wayne Memorial 13 |
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| Oct. 22, 1999 Weekend |
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| Adrian 35, Monroe 14 |
* |
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| Belleville 21, Romulus 20 |
* |
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| Lincoln Park 25, Southgate Anderson 0 |
* |
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| Warren De La Salle 32, Dearborn Fordson 7 |
* |
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| Westland Glenn 24, Wayne Memorial 7 |
* |
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| Wyandotte 35, Dearborn 21 |
* |
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| Ypsilanti 28, Dearborn Edsel Ford 6 |
* |
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| |
| Oct. 29, 1999 Weekend |
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| Detroit Henry Ford 40, Belleville 25 |
* |
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PRE-DISTRICT |
| Westland Glenn 26, Monroe 14 |
* |
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PRE-DISTRICT |
| Ypsilanti 13, Pinckney 7 |
* |
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PRE-DISTRICT |
| |
| Nov. 5, 1999 Weekend |
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| Adrian 28, Ypsilanti 6 |
* |
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DISTRICT FINAL |
* indicates that game is non-conference
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