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| 5/3/2019 | Luxy Raceway - Luxemburg, WI Season Opener Stock Cars, A Modifieds, B Modifieds, Street Stocks, Sport Compact | Results | | Kyle Caswell (Street Stocks) | 5th | - | - | 6th |
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| 5/11/2019 | 141 Speedway - Maribel, WI Mother’s Day Weekend PLUS RED RACE of the Red, White, and Blue Series for Modifieds Stock Cars, Sportsmans, A Modifieds, B Modifieds, Street Stocks, Sport Compact | Results | | Kyle Caswell (Sportsmans) | 6th | - | 1st | 11th |
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| 5/25/2019 | 141 Speedway - Maribel, WI Nathan Bouche Memorial Stock Car Triple Creek Series Night 1 Stock Cars, Sportsmans, A Modifieds, B Modifieds, Street Stocks, Sport Compact | Results | | Kyle Caswell (Sportsmans) | 8th | - | 4th | 17th |
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| 5/31/2019 | Luxy Raceway - Luxemburg, WI Veterans Night Stock Cars, A Modifieds, B Modifieds, Street Stocks, Sport Compact | Results | | Kyle Caswell (Street Stocks) | 6th | - | - | 3rd |
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| 6/8/2019 | 141 Speedway - Maribel, WI Dorsch Ford Lincoln Kia Night PLUS White Race of the Red, White, and Blue Series for Modifides Stock Cars, Sportsmans, A Modifieds, B Modifieds, Street Stocks, Sport Compact | Results | | Kyle Caswell (Sportsmans) | 8th | - | 8th | - |
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| 6/15/2019 | 141 Speedway - Maribel, WI Prestige Custom Cabinets PLUS Go-carts and Spectator Eliminators Stock Cars, Sportsmans, A Modifieds, B Modifieds, Street Stocks, Sport Compact | Results | | Kyle Caswell (Sportsmans) | 4th | - | - | 20th |
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| 6/21/2019 | Luxy Raceway - Luxemburg, WI Regular Race Night Stock Cars, A Modifieds, B Modifieds, Street Stocks, Sport Compact | Results | | Kyle Caswell (Street Stocks) | 3rd | - | - | 3rd |
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| 6/29/2019 | 141 Speedway - Maribel, WI Toby K’s Hideaway Marshalltown Speedway Night PLUS FIREWORKS Stock Cars, Sportsmans, A Modifieds, B Modifieds, Street Stocks, Sport Compact | Results | | Kyle Caswell (Sportsmans) | 4th | - | - | 3rd |
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| 7/6/2019 | 141 Speedway - Maribel, WI Christmas in July, St Jude’s Night Triple Creek Series Night 2 Stock Cars, Sportsmans, A Modifieds, B Modifieds, Street Stocks, Sport Compact | Results | | Kyle Caswell (Sportsmans) | 10th | - | 7th | - |
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| 7/13/2019 | 141 Speedway - Maribel, WI Pepsi Fan Appreciation Night with Corn Roast After Races Stock Cars, Sportsmans, A Modifieds, B Modifieds, Street Stocks, Sport Compact | Results | | Kyle Caswell (Sportsmans) | 2nd | - | - | 18th |
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| 7/18/2019 | 141 Speedway - Maribel, WI King of the Creek II $5,000.00 to Win IMCA Stock Cars Championship Night Stock Cars, Sportsmans, B Modifieds, Street Stocks | Results | | Kyle Caswell (Sportsmans) | 3rd | - | - | 10th |
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| 7/27/2019 | 141 Speedway - Maribel, WI FZE Manufacturing Solutions Presents the Powder Puff Races Stock Cars, Sportsmans, A Modifieds, B Modifieds, Street Stocks, Sport Compact | Results | | Kyle Caswell (Sportsmans) | 7th | - | 8th | - |
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| 8/15/2019 | 141 Speedway - Maribel, WI Inaugural Captain of the Creek $5,000.00 to win for IMCA SportMods Sportsmans, B Modifieds, Street Stocks | Results | | Kyle Caswell (Sportsmans) | 3rd | - | - | 13th |
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| 8/24/2019 | 141 Speedway - Maribel, WI Gandrud Chevy Presents Season Championship Night Stock Cars, Sportsmans, A Modifieds, B Modifieds, Street Stocks, Sport Compact | Results | | Kyle Caswell (Sportsmans) | 7th | - | 3rd | - |
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| 8/30/2019 | Luxy Raceway - Luxemburg, WI Regular Race Night Stock Cars, A Modifieds, B Modifieds, Street Stocks, Sport Compact | Results | | Kyle Caswell (Street Stocks) | 3rd | - | - | 4th |
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| 9/1/2019 | 141 Speedway - Maribel, WI 410 Sprints - Winged: IRA Interstate Racing Association Stock Cars, Sportsmans, Pro Legends | Results | | Kyle Caswell (Sportsmans) | 5th | - | - | 14th |
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| 9/7/2019 | Wilmot Raceway - Wilmot, WI Non Wing Crate Sprints: Wisconsin wingLESS Sprints A Modifieds, Street Stocks, Dirt Late Models | Results | | Kyle Caswell (Street Stocks) | 3rd | - | - | 4th |
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| 9/27/2019 | 141 Speedway - Maribel, WI 10th Annual Creek Classic Stock Cars, Sportsmans, A Modifieds, B Modifieds, Street Stocks, Sport Compact | Results | | Kyle Caswell (Sportsmans) | 3rd | - | - | 18th |
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