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| 5/13/2023 | Charleston Speedway - Charleston, IL Mother's Day Special + Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, 600cc Modifieds, DIRTcar Pro Modifieds | Rain Out |
| 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 | | Jesse Bayless (DIRTcar UMP Modifieds) | 10th | - | - | DNS |
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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 | | Jesse Bayless (DIRTcar UMP Modifieds) | 6th | - | - | 10th |
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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 | | Jesse Bayless (DIRTcar UMP Modifieds) | 7th | - | - | 12th |
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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 | | Jesse Bayless (DIRTcar UMP Modifieds) | 7th | - | - | 14th |
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| 7/8/2023 | Lincoln Park Speedway - Putnamville, IN MSCS Sprints, Modifieds, Super Stocks, Bombers, and MMSA 410 Sprints - Non-Winged: Midwest Sprint Car Series MSCS DIRTcar UMP Modifieds, Factory Stocks, Super Stocks | Results | | Jesse Bayless (DIRTcar UMP Modifieds) | 7th | - | - | 15th |
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| 7/15/2023 | Charleston Speedway - Charleston, IL The 38 Special for DIRTcar Modified presented by Leaf Tree Service. DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Jesse Bayless (DIRTcar UMP Modifieds) | 8th | - | 5th | - |
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| 8/4/2023 | Farmer City Raceway - Farmer City, IL 9th Annual What Up Dog Dirt Super Late Models, DIRTcar UMP Modifieds, Street Stocks, DIRTcar Pro Modifieds, DIRTcar Pro Late Models | Results | | Jesse Bayless (DIRTcar UMP Modifieds) | 9th | - | 7th | - |
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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 | | Jesse Bayless (DIRTcar UMP Modifieds) | DNS | - | 7th | - |
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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 | | Jesse Bayless (DIRTcar UMP Modifieds) | 9th | - | 13th | - |
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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 | | Jesse Bayless (DIRTcar UMP Modifieds) | 8th | - | 5th | 17th (DNF) |
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| 8/26/2023 | Lincoln Park Speedway - Putnamville, IN Saturday Night Racing Lightning Sprints: Midwest Mini Sprint Association DIRTcar UMP Modifieds, Factory Stocks, 410 Sprints - Non-Winged, Super Stocks | Results | | Jesse Bayless (DIRTcar UMP Modifieds) | 7th | - | 8th | - |
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