| Sectional 1 @ Roosevelt Junior High
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| Host: Dolton Roosevelt Date: Wednesday, December 11, 2019
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| Lockport Kelvin Grove def. Glenwood Brookwood
, 46-44 | Lockport Kelvin Grove record now  17-5 | 
| Sectional 2 @ Washington Middle School
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| Host: Washington MS Date: Wednesday, December 11, 2019
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| Germantown Hills def. Wenona Fieldcrest
, 28-19 | Germantown Hills record now  20-3 | 
| Sectional 3 @ Mercer County Jr High
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| Host: Joy Mercer County Date: Wednesday, December 11, 2019
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| Glasford Illini Bluffs def. Sherrard JHS
, 30-15 | Glasford Illini Bluffs record now  23-1 | 
| Sectional 4 @ Peotone Junior High School
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| Host: Peotone Date: Wednesday, December 11, 2019
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| Peotone def. Forrest Prairie Central
, 32-18 | Peotone record now  24-1 | 
| Sectional 5 @ Teutopolis Junior High School
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| Host: Teutopolis Date: Wednesday, December 11, 2019
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| Robinson Nuttall def. Tolono Unity
, 22-21 | Robinson Nuttall record now  22-1 | 
| Sectional 6 @ Olympia Middle School
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| Host: Stanford Olympia Date: Wednesday, December 11, 2019
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| Downs Tri-Valley def. Warrensburg-Latham
, 25-13 | Downs Tri-Valley record now  18-5 | 
| Sectional 7 @ Pleasant Plains Middle School
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| Host: Pleasant Plains Date: Wednesday, December 11, 2019
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| Pleasant Plains def. Camp Point Central
, 19-15 | Pleasant Plains record now  22-1 | 
| Sectional 8 @ Vandalia Junior High School
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| Host: Vandalia Date: Wednesday, December 11, 2019
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| Roxana def. Hillsboro
, 40-29
 OT | Roxana record now  21-3 |