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| 9/13/2020 | Windy Hollow Speedway - Owensboro, KY King of the Hollow! $1,000 win in 4 classes, $500 win Scrappers Hobby Stocks, Stock Cars, Hornets, Pony Stock, Pure Stock | Results | | Gaige Leinenweaver (Pony Stock) | - | - | - | - |
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| 9/20/2020 | Windy Hollow Speedway - Owensboro, KY Racer Appreciation Plus B-Mods! Hobby Stocks, Stock Cars, B Modifieds, Hornets, Pony Stock, Pure Stock | Results | | Gaige Leinenweaver (Pony Stock) | - | - | - | 9th |
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| 9/27/2020 | Windy Hollow Speedway - Owensboro, KY 49 and holding? $490 to win Cruisers! Plus $100 added to all other winners! Hobby Stocks, Stock Cars, Hornets, Pony Stock, Pure Stock | Results | | Gaige Leinenweaver (Pony Stock) | - | - | - | 8th |
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| 10/4/2020 | Windy Hollow Speedway - Owensboro, KY Run for the Gold! Our 50th Anniversary Event! Hobby Stocks, Stock Cars, Hornets, Pony Stock, Pure Stock | Results | | Gaige Leinenweaver (Pony Stock) | - | - | - | 7th |
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| 11/8/2020 | Windy Hollow Speedway - Owensboro, KY Enduro and Scrapper Nationals! DIRTcar UMP Modifieds, Hobby Stocks, Stock Cars, Hornets, Pony Stock, Pure Stock | Canceled |
| 11/28/2020 | Windy Hollow Speedway - Owensboro, KY Enduros, Chain Races and More DIRTcar Factory Stock, B Modifieds, Pony Stock, Sport Compact | No Results |