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| 4/14/2023 | Farmer City Raceway - Farmer City, IL Full Show + Pro Mods + Kid Mods. Dirt Super Late Models, DIRTcar UMP Modifieds, Street Stocks, DIRTcar Pro Modifieds, DIRTcar Pro Late Models | Results | | Kaleb Stephens (DIRTcar Pro Modifieds) | 7th | - | - | 14th |
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| 4/29/2023 | Charleston Speedway - Charleston, IL 60th Annual Season Opener! +6 Divisions of Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Kaleb Stephens (DIRTcar Pro Modifieds) | 7th | - | - | 11th |
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| 5/6/2023 | Charleston Speedway - Charleston, IL Weekly Championship Auto Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Kaleb Stephens (DIRTcar Pro Modifieds) | 5th | - | - | 8th |
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| 5/20/2023 | Charleston Speedway - Charleston, IL Graves 40 DIRTcar Late Models: MARS - Midwest Auto Racing Series DIRTcar UMP Modifieds, Street Stocks, DIRTcar Pro Modifieds | Results | | Kaleb Stephens (DIRTcar Pro Modifieds) | 5th | - | - | 10th |
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| 5/27/2023 | Charleston Speedway - Charleston, IL Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Kaleb Stephens (DIRTcar Pro Modifieds) | 5th | - | - | 13th |
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| 6/3/2023 | Charleston Speedway - Charleston, IL Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Kaleb Stephens (DIRTcar Pro Modifieds) | 3rd | - | - | 7th |
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| 6/10/2023 | Charleston Speedway - Charleston, IL Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Kaleb Stephens (DIRTcar Pro Modifieds) | 5th | - | - | 7th |
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| 6/17/2023 | Charleston Speedway - Charleston, IL Father's Day Special + Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, 600cc Modifieds, DIRTcar Pro Modifieds | Results | | Kaleb Stephens (DIRTcar Pro Modifieds) | 3rd | - | - | 14th |
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| 6/24/2023 | Charleston Speedway - Charleston, IL Summer Shootout Double Points Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Kaleb Stephens (DIRTcar Pro Modifieds) | 4th | - | - | 8th |
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| 8/5/2023 | Charleston Speedway - Charleston, IL Fan Appreciation Night + Driver Autographs + Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, 600cc Modifieds, DIRTcar Pro Modifieds | Results | | Kaleb Stephens (DIRTcar Pro Modifieds) | 5th | - | - | 11th |
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| 8/12/2023 | Charleston Speedway - Charleston, IL Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Kaleb Stephens (DIRTcar Pro Modifieds) | 7th | - | - | 10th |
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| 8/19/2023 | Charleston Speedway - Charleston, IL Driver Appreciation Night + Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, 600cc Modifieds, DIRTcar Pro Modifieds | Results | | Kaleb Stephens (DIRTcar Pro Modifieds) | 3rd | - | - | 14th |
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| 9/2/2023 | Charleston Speedway - Charleston, IL 4th Annual Freaky 40 for Pro Modified presented by McHugh's Double Drive Thru + Add'l Classes DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Kaleb Stephens (DIRTcar Pro Modifieds) | 3rd | - | - | 14th |
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| 9/9/2023 | Federated Auto Parts I-55 Raceway - Pevely, MO Weekly Racing DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, DIRTcar Sport Compact, B Modifieds | Results | | Kaleb Stephens (B Modifieds) | 9th | - | - | 20th |
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| 9/16/2023 | Charleston Speedway - Charleston, IL Double Down Sizzler for Double Championship Points DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Kaleb Stephens (DIRTcar Pro Modifieds) | 5th | - | - | 7th |
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| 10/7/2023 | Charleston Speedway - Charleston, IL Season Finale + Powderpuff & Mechanic Races DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, Generic 1, Generic 2, DIRTcar Pro Modifieds, Ladies - Bombers, Ladies - Factory Stock | Results | | Kaleb Stephens (DIRTcar Pro Modifieds) | 4th | - | - | 12th |
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