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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 | | Jesse Simmons (Street Stocks) | 3rd | - | - | 10th |
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| 4/9/2021 | Farmer City Raceway - Farmer City, IL Weekly night plus Pro Mods DIRTcar UMP Modifieds, Street Stocks, Dirt Late Models, Pro Late Model, DIRTcar Pro Modifieds | Results | | Jesse Simmons (Street Stocks) | 4th | - | - | 9th |
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| 4/16/2021 | Farmer City Raceway - Farmer City, IL Friday Weekly Races DIRTcar UMP Modifieds, Street Stocks, Dirt Late Models, Hornets, Pro Late Model | Results | | Jesse Simmons (Street Stocks) | 5th | - | - | 4th |
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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 | | Jesse Simmons (Street Stocks) | 2nd | - | - | 13th (DNF) |
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| 5/7/2021 | Farmer City Raceway - Farmer City, IL Full Show Plus Hornets DIRTcar UMP Modifieds, Street Stocks, Dirt Late Models, Hornets, Pro Late Model | Results | | Jesse Simmons (Street Stocks) | 2nd | - | - | 10th |
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| 5/8/2021 | Fairbury Speedway - Fairbury, IL FALS Cup Weekly Racing DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Street Stocks | Results | | Jesse Simmons (Street Stocks) | 1st | - | - | - |
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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 | | Jesse Simmons (Street Stocks) | 3rd | - | - | 10th |
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| 5/22/2021 | Fairbury Speedway - Fairbury, IL FALS Cup Weekly Racing DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Street Stocks | Results | | Jesse Simmons (Street Stocks) | 3rd | - | - | 5th |
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| 5/29/2021 | Fairbury Speedway - Fairbury, IL FALS Cup Weekly Racing, Earl J Hubert Memorial Street Stock Special DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, Street Stocks, Pro Late Model | Results | | Jesse Simmons (Street Stocks) | 5th | - | 3rd | - |
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| 5/31/2021 | Macon Speedway - Macon, IL Memorial Day Twin 50s - SLM 50 laps & Modifieds 50 laps DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets | Results | | Jesse Simmons (Street Stocks) | 3rd | - | - | 11th |
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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 | | Jesse Simmons (Street Stocks) | 7th | - | - | 2nd |
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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 |
| 6/18/2021 | Farmer City Raceway - Farmer City, IL Weekly show Plus Vintage Cars DIRTcar UMP Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Jesse Simmons (Street Stocks) | 2nd | - | - | 2nd |
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| 7/2/2021 | Farmer City Raceway - Farmer City, IL Fan Appreciation/Full Show DIRTcar UMP Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Jesse Simmons (Street Stocks) | 1st | - | - | 2nd |
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| 7/3/2021 | Fairbury Speedway - Fairbury, IL FALS Cup Weekly Racing plus Fireworks. Emergency First Responder Night DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Street Stocks | Results | | Jesse Simmons (Street Stocks) | 5th | - | - | 7th |
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| 7/4/2021 | East Moline Speedway - East Moline, IL Weekly Racing Street Stocks, IMCA Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock, Mod Lites | Results | | Jesse Simmons (Street Stocks) | 2nd | - | - | 1st |
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| 7/17/2021 | Fairbury Speedway - Fairbury, IL FALS Cup Weekly Racing, Eden/Piercy Memorial Sportsman Special DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Street Stocks | Results | | Jesse Simmons (Street Stocks) | 7th | - | 1st | 10th |
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| 7/23/2021 | Farmer City Raceway - Farmer City, IL Jr. Kimler Memorial Race DIRTcar UMP Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Jesse Simmons (Street Stocks) | 1st | - | - | 4th |
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| 7/25/2021 | Lincoln Speedway - Lincoln, IL USAC Engler IMRA SpeeD2 Midgets 410 Sprints - Winged, Economy Midgets, DIRTcar UMP Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Jesse Simmons (Street Stocks) | 6th | - | - | 11th |
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| 9/5/2021 | East Moline Speedway - East Moline, IL R.T. Fallen Hero's Street Stock Memorial Plus Nostalgia (classes TBD) Street Stocks, Vintage Full Body Stock Cars, Sport Compact, IMCA Modified, IMCA Northern SportMod | Results | | Jesse Simmons (Street Stocks) | 4th | - | 4th | 6th |
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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 | | Jesse Simmons (Street Stocks) | 1st | - | - | 2nd |
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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 | | Jesse Simmons (Street Stocks) | 2nd | - | - | 6th |
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| 10/1/2021 | Lincoln Speedway - Lincoln, IL DIRTcar Fall Nationals DIRTcar UMP Modifieds, DIRTcar Pro Modifieds, DIRTcar Stock Car, DIRTcar Pro Late Models | Results | | Jesse Simmons (DIRTcar Stock Car) | 1st | - | - | 6th |
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| 10/9/2021 | Charleston Speedway - Charleston, IL UMP FALL NATIONALS for STREET STOCK & FACTORY STOCKS DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, 600cc Modifieds | Results | | Jesse Simmons (Street Stocks) | 4th | - | - | 10th (DNF) |
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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 | | Jesse Simmons (Street 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 | | Jesse Simmons (Street Stocks) | 2nd | - | - | 1st |
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