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| 4/14/2023 | Kankakee County Speedway - Kankakee, IL Lee J. Hall Memorial + DIRTcar Pro Late Model Special DIRTcar UMP Modifieds, DIRTcar Factory Stock, DIRTcar Sport Compact, DIRTcar Pro Modifieds, DIRTcar Stock Car, DIRTcar Pro Late Models | Results | | Mike Winn (DIRTcar Pro Late Models) | - | 6th | - | 15th (DNF) |
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| 4/21/2023 | Kankakee County Speedway - Kankakee, IL DIRTcar Modified Special + Crown Victorias DIRTcar UMP Modifieds, DIRTcar Factory Stock, DIRTcar Sport Compact, Stock Cars, DIRTcar Pro Modifieds, DIRTcar Stock Car, DIRTcar Pro Late Models | Results | | Mike Winn (DIRTcar Pro Late Models) | 11th | - | - | 17th |
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| 4/28/2023 | 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 | | Mike Winn (DIRTcar Pro Late Models) | 9th | - | - | 8th (DNF) |
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| 5/26/2023 | Kankakee County Speedway - Kankakee, IL DIRTcar Sport Compact Special + Big Wheel Races + Crown Victorias DIRTcar Factory Stock, DIRTcar Sport Compact, Stock Cars, DIRTcar Pro Modifieds, DIRTcar Stock Car, DIRTcar Pro Late Models | Results | | Mike Winn (DIRTcar Pro Late Models) | 8th | - | - | 17th (DNF) |
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| 5/27/2023 | Fairbury Speedway - Fairbury, IL $5,000-To-Win MARS Super Late Models; $2,000-To-Win MARS Modifieds DIRTcar Late Models: MARS - Midwest Auto Racing Series Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, Pro Late Model | Results | | Mike Winn (Pro Late Model) | 10th | - | 15th | - |
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| 7/21/2023 | Kankakee County Speedway - Kankakee, IL Dick Potts Memorial $2000 to Win DIRTcar Pro Late Models DIRTcar UMP Modifieds, DIRTcar Factory Stock, DIRTcar Sport Compact, DIRTcar Pro Modifieds, DIRTcar Stock Car, DIRTcar Pro Late Models | Results | | Mike Winn (DIRTcar Pro Late Models) | 6th | - | - | 17th (DNF) |
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| 7/23/2023 | Lincoln Speedway - Lincoln, IL Sunday Funday DIRTcar UMP Modifieds, DIRTcar Sport Compact, Sportsmans, Street Stocks, Badger Midgets, DIRTcar Pro Late Models | Rain Out |
| 8/2/2023 | Kankakee County Speedway - Kankakee, IL Fair Night Racing DIRTcar UMP Modifieds, DIRTcar Sport Compact, DIRTcar Pro Late Models | Results | | Mike Winn (DIRTcar Pro Late Models) | 5th | - | - | 9th |
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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 | | Mike Winn (DIRTcar Pro Late Models) | 6th | - | 10th | - |
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| 8/11/2023 | Farmer City Raceway - Farmer City, IL Full Show +Pro Mods. Dirt Super Late Models, DIRTcar UMP Modifieds, Street Stocks, DIRTcar Pro Modifieds, DIRTcar Pro Late Models | Results | | Mike Winn (DIRTcar Pro Late Models) | 6th | - | - | 12th |
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| 8/18/2023 | Kankakee County Speedway - Kankakee, IL DIRTcar Stock Car Special + Power Wheel Races DIRTcar UMP Modifieds, DIRTcar Factory Stock, DIRTcar Sport Compact, Stock Cars, DIRTcar Pro Modifieds, DIRTcar Stock Car, DIRTcar Pro Late Models | Results | | Mike Winn (DIRTcar Pro Late Models) | 6th | - | - | 8th |
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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 | | Mike Winn (Dirt Late Models) | 6th | - | - | 14th (DNF) |
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| 8/25/2023 | Kankakee County Speedway - Kankakee, IL Vintage Racing of Illinois + DIRTcar Pro Modified Special + Kids Power Wheels Races DIRTcar UMP Modifieds, DIRTcar Factory Stock, DIRTcar Sport Compact, Stock Cars, Vintage Full Body Stock Cars, DIRTcar Pro Modifieds, DIRTcar Stock Car, DIRTcar Pro Late Models | Results | | Mike Winn (DIRTcar Pro Late Models) | 5th | - | - | 13th |
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| 8/26/2023 | Fairbury Speedway - Fairbury, IL FALS Cup Weekly Racing Championship Night DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Street Stocks | Results | | Mike Winn (DIRTcar Late Models) | 7th | - | 5th | - |
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| 9/1/2023 | Farmer City Raceway - Farmer City, IL $5,000-To-Win MARS Super Late Models; $2,000-To-Win MARS Modifieds DIRTcar Late Models: MARS - Midwest Auto Racing Series DIRTcar UMP Modifieds, Street Stocks, DIRTcar Pro Late Models | Results | | Mike Winn (DIRTcar Pro Late Models) | 7th | - | - | 13th |
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| 9/2/2023 | Fairbury Speedway - Fairbury, IL $5,000-To-Win MARS Super Late Models; $5,000-To-Win MARS Modifieds DIRTcar Late Models: MARS - Midwest Auto Racing Series DIRTcar UMP Modifieds, A Modifieds, Pro Late Model | Results | | Mike Winn (Pro Late Model) | 10th | - | 7th | - |
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| 9/8/2023 | Spoon River Speedway - Canton, IL HART E-Mods & Hornet Nationals - Qualifying Night Limited Modified, DIRTcar Pro Late Models, DIRTcar 4 Cylinders | Results | | Mike Winn (DIRTcar Pro Late Models) | 3rd | - | - | 5th |
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| 9/15/2023 | Kankakee County Speedway - Kankakee, IL $5,000-To-Win MARS Super Late Models DIRTcar UMP Modifieds, DIRTcar Factory Stock, DIRTcar Sport Compact, Stock Cars, DIRTcar Pro Modifieds, DIRTcar Stock Car, DIRTcar Pro Late Models | Results | | Mike Winn (DIRTcar Pro Late Models) | 7th | - | - | 13th (DNF) |
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| 9/22/2023 | Kankakee County Speedway - Kankakee, IL Championship Night Presented by Taylor Cars DIRTcar UMP Modifieds, DIRTcar Factory Stock, DIRTcar Sport Compact, Stock Cars, DIRTcar Pro Modifieds, DIRTcar Stock Car, DIRTcar Pro Late Models | Results | | Mike Winn (DIRTcar Pro Late Models) | 6th | - | - | 14th |
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| 9/23/2023 | Spoon River Speedway - Canton, IL Season Championship Midgets: POWRi DIRTcar UMP Modifieds, B Modifieds, DIRTcar Pro Late Models, DIRTcar 4 Cylinders | Results | | Mike Winn (DIRTcar Pro Late Models) | 1st | - | - | 5th |
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| 10/7/2023 | Fairbury Speedway - Fairbury, IL World of Outlaws FALS Frenzy Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Late Models: MARS - Midwest Auto Racing Series DIRTcar UMP Modifieds, Dirt Late Models, Pro Late Model | Results | | Mike Winn (Pro Late Model) | 10th | - | - | DNS |
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