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| 4/2/2021 | Farmer City Raceway - Farmer City, IL Triple Qualifying Features $600 to win $100 to start Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds: Summit American Modified Series Street Stocks, Dirt Late Models, Pro Late Model | Results | | Kenny Carmichael Sr (DIRTcar UMP Modifieds) | 14th | - | - | - |
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| 4/3/2021 | Farmer City Raceway - Farmer City, IL $2500 to win $150 to start Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds: Summit American Modified Series Dirt Late Models, Pro Late Model | Results | | Kenny Carmichael Sr (DIRTcar UMP Modifieds) | - | - | DNS | - |
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| 5/1/2021 | Charleston Speedway - Charleston, IL FIRST Night for UMP and Track Points DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Hornets, 600cc Modifieds, DIRTcar Pro Modifieds | Results | | Kenny Carmichael Sr (DIRTcar UMP Modifieds) | 1st | - | - | 4th |
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| 5/15/2021 | Charleston Speedway - Charleston, IL WEEKLY RACING DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Hornets, DIRTcar Pro Modifieds | Results | | Kenny Carmichael Sr (DIRTcar UMP Modifieds) | 4th | - | - | 5th |
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| 5/22/2021 | Lincoln Park Speedway - Putnamville, IN Saturday Night Racing DIRTcar UMP Modifieds, Factory Stocks, 410 Sprints - Non-Winged, Super Stocks | Results | | Kenny Carmichael Sr (Super Stocks) | 3rd | - | - | 9th |
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| 5/29/2021 | Lincoln Park Speedway - Putnamville, IN MSCS SPRINTS $2,500 to win 410 Sprints - Non-Winged: Midwest Sprint Car Series MSCS DIRTcar UMP Modifieds, Factory Stocks, Super Stocks | Results | | Kenny Carmichael Sr (Super Stocks) | 8th | - | 1st | 16th |
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| 6/5/2021 | Charleston Speedway - Charleston, IL WEEKLY RACING DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Hornets, DIRTcar Pro Modifieds | Results | | Kenny Carmichael Sr (DIRTcar UMP Modifieds) | 8th (DNF) | - | - | 20th (DNF) |
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| 6/11/2021 | Charleston Speedway - Charleston, IL POWRi Lucas Oil WAR Sprints at Charleston Speedway Non-Winged Sprints: POWRi WAR Sprints Midgets, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Kenny Carmichael Sr (Dirt Late Models) | 3rd | - | - | 3rd |
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| 6/12/2021 | Charleston Speedway - Charleston, IL WEEKLY RACING DIRTcar UMP Modifieds, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Rain Out |
| 7/2/2021 | Lincoln Park Speedway - Putnamville, IN Bill Gardner Sprintacular Night 1 with MSCS/USAC Sprints 410 Sprints - Non-Winged: USAC National Sprint Cars with Midwest Sprint Car Series MSCS DIRTcar UMP Modifieds, Factory Stocks, Super Stocks | Results | | Kenny Carmichael Sr (Super Stocks) | 3rd | - | - | 13th |
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| 7/18/2021 | Terre Haute Action Track - Terre Haute, IN Vigo County Fair with American Modified Series and Indiana super stocks DIRTcar UMP Modifieds: DIRTcar Modified Nationals with Summit American Modified Series Super Stocks | Results | | Kenny Carmichael Sr (DIRTcar UMP Modifieds) | 3rd | - | - | 11th | | Kenny Carmichael Sr (Super Stocks) | DNS | - | - | DNS |
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| 7/24/2021 | Charleston Speedway - Charleston, IL WEEKLY RACING DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Kenny Carmichael Sr (DIRTcar UMP Modifieds) | 1st | - | - | 3rd | | Kenny Carmichael Sr (Dirt Late Models) | 4th | - | - | 3rd |
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| 7/31/2021 | Charleston Speedway - Charleston, IL J. Smith & T. Robertson Productions $1,500 to win Sprints Plus Weekly Racing DIRTcar UMP Modifieds, Street Stocks, Dirt Late Models, 410 Sprints - Non-Winged, Hornets, DIRTcar Pro Modifieds | Results | | Kenny Carmichael Sr (DIRTcar UMP Modifieds) | 2nd | - | - | 7th | | Kenny Carmichael Sr (Dirt Late Models) | 3rd | - | - | 5th |
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| 8/7/2021 | Charleston Speedway - Charleston, IL DRIVERS AUTOGRAPH NIGHT DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Kenny Carmichael Sr (DIRTcar UMP Modifieds) | 4th | - | - | 9th | | Kenny Carmichael Sr (Dirt Late Models) | 1st | - | - | 1st |
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| 8/14/2021 | Charleston Speedway - Charleston, IL WEEKLY RACING DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Hornets, 600cc Modifieds, DIRTcar Pro Modifieds | Results | | Kenny Carmichael Sr (DIRTcar UMP Modifieds) | 6th | - | - | 5th |
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| 8/21/2021 | Charleston Speedway - Charleston, IL WEEKLY RACING DIRTcar UMP Modifieds, Street Stocks, Dirt Late Models, Hornets, 600cc Modifieds, DIRTcar Pro Modifieds | Results | | Kenny Carmichael Sr (DIRTcar UMP Modifieds) | 4th | - | - | 12th (DNF) | | Kenny Carmichael Sr (Dirt Late Models) | 2nd | - | - | 1st |
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| 8/28/2021 | Charleston Speedway - Charleston, IL Leaf Tree Service presents The .38 SPECIAL for UMP MODIFIEDS!! DIRTcar UMP Modifieds, DIRTcar Factory Stock, Hornets | Results | | Kenny Carmichael Sr (DIRTcar UMP Modifieds) | 5th | - | 1st | 13th |
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| 9/5/2021 | Circle City Raceway - Indianapolis, IN Crate Late Models, UMP Modifieds, Steel Block Sprint Cars, Fords, Legends DIRTcar UMP Modifieds, 410 Sprints - Non-Winged, Pro Legends, Dirt Crate Late Models, Crown Vic | Results | | Kenny Carmichael Sr (Dirt Crate Late Models) | 6th | - | - | 17th |
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| 9/11/2021 | Charleston Speedway - Charleston, IL WEEKLY RACING DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Hornets, DIRTcar Pro Modifieds | Results | | Kenny Carmichael Sr (DIRTcar UMP Modifieds) | 6th | - | - | 8th |
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| 9/18/2021 | Charleston Speedway - Charleston, IL $2k to WIN, $100 to start Freaky 40 by Fencing Freaks for Pro Modified DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Rain Out |
| 9/25/2021 | Charleston Speedway - Charleston, IL DOUBLE POINTS -and- CHAMPIONSHIP NIGHT DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Kenny Carmichael Sr (DIRTcar UMP Modifieds) | 5th | - | - | 4th | | Kenny Carmichael Sr (Dirt Late Models) | 2nd | - | - | 2nd |
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| 10/16/2021 | Kokomo Speedway - Kokomo, IN Kokomo Klash XV 305 Sprints - Winged, Dirt Super Late Models, A Modifieds, Street Stocks, Hornets, Super Stocks | Results | | Kenny Carmichael Sr (A Modifieds) | - | - | - | - | | Kenny Carmichael Sr (Super Stocks) | - | - | - | - |
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| 10/23/2021 | Charleston Speedway - Charleston, IL TRUNK or TREAT Night + Powder Puff & Mechanics Race DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Kenny Carmichael Sr (DIRTcar UMP Modifieds) | 3rd | - | - | 4th | | Kenny Carmichael Sr (Dirt Late Models) | 1st | - | - | 3rd |
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