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| 4/15/2023 | Western Kentucky Speedway - Madisonville, KY Opening Night of Racing Factory Stocks, Hobby Stocks, Hornets, CRUSA Street Stocks | Results | | Jacob Richmond (Hobby Stocks) | 1st | - | - | 5th |
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| 5/6/2023 | Western Kentucky Speedway - Madisonville, KY 3rd Annual Spring Fling Factory Stocks, Hobby Stocks, B Modifieds, Hornets, CRUSA Street Stocks | Results | | Jacob Richmond (Factory Stocks) | 7th | - | - | DNS | | Jacob Richmond (Hobby Stocks) | 1st | - | - | 12th |
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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 | | Jacob Richmond (Stock Cars) | 1st | - | - | 1st | | Jacob Richmond (Pure Stock) | 3rd | - | - | 7th |
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| 5/27/2023 | Western Kentucky Speedway - Madisonville, KY Kentucky Top Dog Street Stock Series Factory Stocks, Hobby Stocks, Street Stocks, Hornets, CRUSA Street Stocks | Results | | Jacob Richmond (Factory Stocks) | 3rd | - | - | 6th | | Jacob Richmond (Hobby Stocks) | 7th | - | - | 13th |
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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 | | Jacob Richmond (Stock Cars) | 1st | - | - | 1st |
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| 6/4/2023 | Windy Hollow Speedway - Owensboro, KY BATTLE OF THE HORNETS $2500 TO WIN MINI STOCKS Hobby Stocks, Stock Cars, B Modifieds, Hornets, CRUSA Street Stocks, Pure Stock | Results | | Jacob Richmond (Stock Cars) | 2nd | - | - | 2nd | | Jacob Richmond (Pure Stock) | 3rd | - | - | 2nd |
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| 6/10/2023 | Western Kentucky Speedway - Madisonville, KY Dustin Ray Memorial Factory Stocks, Hobby Stocks, Hornets, CRUSA Street Stocks | Results | | Jacob Richmond (Factory Stocks) | 2nd | - | - | 1st | | Jacob Richmond (Hobby Stocks) | 1st | - | - | - |
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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 | | Jacob Richmond (Stock Cars) | 8th | - | - | DNS | | Jacob Richmond (Pure Stock) | 1st | - | - | 6th |
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| 6/23/2023 | Western Kentucky Speedway - Madisonville, KY 5th Annual King of the Bluegrass CRUSA Street Stocks: Ultimate Street Stock Challenge Factory Stocks, Hobby Stocks, Hornets | Results | | Jacob Richmond (Factory Stocks) | 1st | - | - | - |
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| 7/8/2023 | Western Kentucky Speedway - Madisonville, KY $1000 to win UMP Mods DIRTcar UMP Modifieds, Factory Stocks, Hobby Stocks, Hornets, CRUSA Street Stocks | Results | | Jacob Richmond (Factory Stocks) | - | - | - | - | | Jacob Richmond (Hobby Stocks) | 1st | - | - | - |
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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 | | Jacob Richmond (Stock Cars) | 6th | - | - | 2nd |
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| 7/22/2023 | Western Kentucky Speedway - Madisonville, KY $1000 to win UMP Modifieds plus all regular classes DIRTcar UMP Modifieds, Factory Stocks, Hobby Stocks, Hornets, CRUSA Street Stocks | Results | | Jacob Richmond (Factory Stocks) | 1st | - | - | - | | Jacob Richmond (Hobby Stocks) | 1st | - | - | - |
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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 | | Jacob Richmond (Stock Cars) | 1st | - | - | 1st | | Jacob Richmond (Pure Stock) | 1st | - | - | 9th |
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| 8/12/2023 | Western Kentucky Speedway - Madisonville, KY Rusty Bolt Rumble Factory Stocks, Hobby Stocks, Hornets, CRUSA Street Stocks | Results | | Jacob Richmond (Factory Stocks) | 1st | - | - | 1st | | Jacob Richmond (Hobby Stocks) | 1st | - | - | 13th |
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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 | | Jacob Richmond (Stock Cars) | 5th | - | - | DNS | | Jacob Richmond (Pure Stock) | 1st | - | - | 1st |
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| 9/3/2023 | Windy Hollow Speedway - Owensboro, KY KING OF THE ECONOMIES -- $500 TO WIN Hobby Stocks, Stock Cars, B Modifieds, Hornets, CRUSA Street Stocks, Pure Stock | Results | | Jacob Richmond (Stock Cars) | 1st | - | - | 1st | | Jacob Richmond (Pure Stock) | 1st | - | - | 7th |
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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 | | Jacob Richmond (Stock Cars) | 8th | - | - | 5th | | Jacob Richmond (Pure Stock) | 2nd | - | - | DNS |
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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 | | Jacob Richmond (Stock Cars) | 6th | - | - | DNS | | Jacob Richmond (Pure Stock) | 1st | - | - | 1st |
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| 10/21/2023 | Western Kentucky Speedway - Madisonville, KY Fall Classic Factory Stocks, Hobby Stocks, Hornets, CRUSA Street Stocks | Results | | Jacob Richmond (Factory Stocks) | 1st | - | - | 1st |
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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 | | Jacob Richmond (Stock Cars) | - | - | - | 1st |
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