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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 |
| 5/20/2023 | Macon Speedway - Macon, IL 95Q Armed Forces Night (Featuring Free Admission for Active and Retired Military DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Street Stocks, Pro Late Model, Limited Modified | Results | | Kaylynn Eskew (Limited Modified) | 2nd | - | - | 2nd |
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| 5/27/2023 | Red Hill Raceway - Sumner, IL Red Hill Memorial Rumble DIRTcar UMP Modifieds, DIRTcar Factory Stock, Stock Cars, B Modifieds, 600cc Modifieds | Results | | Kaylynn Eskew (600cc Modifieds) | 2nd | - | - | 2nd |
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| 7/15/2023 | Macon Speedway - Macon, IL POWRi Micros at Macon Speedway DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Kaylynn Eskew (B Modifieds) | 7th | - | - | 13th |
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| 8/12/2023 | Macon Speedway - Macon, IL Throwback Sprint Cars / CEFCU Kids Club Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Non-Winged Sprints, Pro Late Model, Limited Modified, Dirt 6-cyl Stock Cars | Results | | Kaylynn Eskew (B Modifieds) | 6th | - | - | 12th |
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| 9/16/2023 | Macon Speedway - Macon, IL KERBYSTRONG Night featuring PLM, Modified, and Sportsman Specials / CEFCU Kids Club DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Hornets, Pro Late Model, HART Non-Wing Micros | Results | | Kaylynn Eskew (B Modifieds) | 8th | - | - | 12th |
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| 9/23/2023 | Macon Speedway - Macon, IL Brandt Season Championship "Racing for the Cup" DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Street Stocks, Hornets, Pro Late Model, Hybrid 600cc Micros | Results | | Kaylynn Eskew (B Modifieds) | 7th | - | 9th | - |
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| 9/28/2023 | Lincoln Speedway - Lincoln, IL Practice Night for DIRTcar Fall Nationals DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Street Stocks, DIRTcar Pro Modifieds, DIRTcar Stock Car, DIRTcar Pro Late Models | Results | | Kaylynn Eskew (DIRTcar Pro Modifieds) | - | - | - | - |
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| 9/29/2023 | Lincoln Speedway - Lincoln, IL DIRTcar Fall Nationals DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Pro Modifieds, DIRTcar Stock Car | Results | | Kaylynn Eskew (DIRTcar Pro Modifieds) | 10th | - | 10th | - |
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| 9/30/2023 | Lincoln Speedway - Lincoln, IL DIRTcar Fall Nationals Night 2 DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Pro Modifieds, DIRTcar Pro Late Models | Results | | Kaylynn Eskew (DIRTcar Pro Modifieds) | 9th | - | DNS | - |
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