| 2025 8th Grade Boys Basketball Contests
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| Regular Season Contests (self-reported) |
| Winchester def. Virginia
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45-25
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| Winchester def. Jacksonville Our Saviour
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50-30
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| Pittsfield Pikeland vs. Winchester
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PENDING
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| Rushville Schuyler Industry vs. Winchester
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PENDING
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| Camp Point Central def. Winchester
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44-36
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| Winchester def. Beardstown MS
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40-29
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| Winchester def. Griggsville-Perry
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35-25
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| Winchester def. White Hall North Greene
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47-19
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| Winchester def. Concord Triopia
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54-40
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| Winchester def. Carrollton GS
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63-36
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| Winchester def. Concord Triopia
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34-15
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| Winchester def. Waverly
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54-47
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| Winchester def. Ashland A-C Central
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53-18
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| Winchester def. White Hall North Greene
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49-31
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| Mt. Sterling Brown County def. Winchester
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41-35
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| Winchester def. Greenview
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52-9
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| Winchester def. Virginia
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48-25
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| Winchester def. Mt. Sterling Brown County
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41-28
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| Winchester def. Carrollton St. John
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48-30
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| Class 8-2A Regional 15 |
| Winchester def. Kincaid South Fork
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75-42
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| Winchester def. New Berlin JHS
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49-38
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| Winchester def. Nokomis JHS
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47-29
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| Class 8-2A Sectional 8 |
| Winchester def. Hardin Calhoun
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39-34
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| Class 8-2A State Tournament |
| Camp Point Central def. Winchester
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48-33
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1st Round
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