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| 5/14/2023 | Windy Hollow Speedway - Owensboro, KY OPENING NIGHT/ MOTHERS DAY SPECIAL $600 TO WIN Hobby Stocks, Stock Cars, B Modifieds, Hornets, CRUSA Street Stocks, Pure Stock | Results | | James Dockery (Pure Stock) | 3rd | - | - | 5th |
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| 5/28/2023 | Windy Hollow Speedway - Owensboro, KY TOP DOG STREET DOG SPECIAL -- $2000 TO WIN Hobby Stocks, Stock Cars, Hornets, CRUSA Street Stocks, Pure Stock, Dirt Crate Late Models | Results | | James Dockery (Pure Stock) | 6th | - | - | 4th |
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| 7/16/2023 | Windy Hollow Speedway - Owensboro, KY SUMMER SIZZLER -- Hobby Stocks, Stock Cars, B Modifieds, Hornets, Pony Stock, CRUSA Street Stocks, Pure Stock | Results | | James Dockery (Hornets) | - | - | - | 2nd | | James Dockery (Pure Stock) | 5th | - | - | 3rd |
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| 7/30/2023 | Windy Hollow Speedway - Owensboro, KY KING OF THE BOMBERS -- $1000 TO WIN -- E-Z AUTO PARTS & SALES SPECIAL Hobby Stocks, Stock Cars, Hornets, CRUSA Street Stocks, Pure Stock, Dirt Crate Late Models | Results | | James Dockery (Hornets) | 1st | - | - | 5th |
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| 10/1/2023 | Windy Hollow Speedway - Owensboro, KY RACE ON MEMORIAL -- $668.08 TO WIN ALL CLASSES Hobby Stocks, Stock Cars, Hornets, CRUSA Street Stocks, Pure Stock, Dirt Crate Late Models | Results | | James Dockery (Stock Cars) | 1st | - | - | 1st | | James Dockery (Pure Stock) | 2nd | - | - | 12th |
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| 10/15/2023 | Windy Hollow Speedway - Owensboro, KY CHAMPIONSHIP NIGHT -- LAST POINTS RACE Hobby Stocks, Stock Cars, Hornets, CRUSA Street Stocks, Pure Stock, Dirt Crate Late Models | Results | | James Dockery (Stock Cars) | 1st | - | - | 7th |
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| 11/26/2023 | Windy Hollow Speedway - Owensboro, KY Turkey Gobbler 100 Lapper DIRTcar Factory Stock, Stock Cars, Hornets, Sport Compact | Results | | James Dockery (Stock Cars) | - | - | - | 7th | | James Dockery (Sport Compact) | - | - | - | 3rd |
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