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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 | | Jamie Bosecker (Dirt Crate Late Models) | 7th | - | - | 3rd |
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| 6/18/2023 | Windy Hollow Speedway - Owensboro, KY KING OF THE RUSTY BOLTS -- $700 TO WIN Hobby Stocks, Stock Cars, Hornets, Pony Stock, CRUSA Street Stocks, Pure Stock, Dirt Crate Late Models | Results | | Jamie Bosecker (Dirt Crate Late Models) | 3rd | - | - | 5th |
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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 | | Jamie Bosecker (Dirt Crate Late Models) | 4th | - | - | 3rd |
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| 8/20/2023 | Windy Hollow Speedway - Owensboro, KY KING OF THE CRATES --- $1000 TO WIN Hobby Stocks, Stock Cars, Hornets, Pony Stock, CRUSA Street Stocks, Pure Stock, Dirt Crate Late Models | Results | | Jamie Bosecker (Dirt Crate Late Models) | 8th | - | - | 4th |
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| 9/17/2023 | Windy Hollow Speedway - Owensboro, KY SCRAPPER YOUNG GUNS SPECIAL -- $250 TO WIN Hobby Stocks, Stock Cars, Hornets, Pony Stock, CRUSA Street Stocks, Pure Stock, Dirt Crate Late Models | Results | | Jamie Bosecker (Dirt Crate Late Models) | 3rd | - | - | 3rd |
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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 | | Jamie Bosecker (Dirt Crate Late Models) | 6th | - | - | 5th |
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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 | | Jamie Bosecker (Dirt Crate Late Models) | 3rd | - | - | 3rd |
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