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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 | | Jesse Simmons (DIRTcar Factory Stock) | 4th | - | - | 22nd | | Jesse Simmons (DIRTcar Sport Compact) | - | - | - | - |
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| 4/21/2023 | 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 | | Jesse Simmons (Street Stocks) | 4th | - | - | 4th |
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| 4/29/2023 | Charleston Speedway - Charleston, IL 60th Annual Season Opener! +6 Divisions of Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Jesse Simmons (Street Stocks) | 3rd | - | - | 1st |
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| 5/5/2023 | Kankakee County Speedway - Kankakee, IL AFS Badger Midget Series Season Opener Badger Midgets: Badger Midget Auto Racing Association with Midget Auto Racing Association DIRTcar UMP Modifieds, DIRTcar Factory Stock, DIRTcar Sport Compact, Non Wing Crate Sprints, DIRTcar Pro Modifieds, DIRTcar Stock Car | Results | | Jesse Simmons (DIRTcar Stock Car) | 4th | - | - | 7th |
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| 5/6/2023 | Charleston Speedway - Charleston, IL Weekly Championship Auto Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Jesse Simmons (Street Stocks) | 5th | - | - | 6th |
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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 | Charleston Speedway - Charleston, IL Graves 40 DIRTcar Late Models: MARS - Midwest Auto Racing Series DIRTcar UMP Modifieds, Street Stocks, DIRTcar Pro Modifieds | Results | | Jesse Simmons (Street Stocks) | 1st | - | - | 2nd |
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| 5/26/2023 | 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 Dirt Super Late Models, DIRTcar UMP Modifieds, Street Stocks, DIRTcar Pro Late Models | Results | | Jesse Simmons (Street Stocks) | 2nd | - | - | 2nd |
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| 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 Simmons (Street Stocks) | 2nd | - | - | 2nd |
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| 6/3/2023 | Charleston Speedway - Charleston, IL Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Jesse Simmons (Street Stocks) | 1st | - | - | 3rd |
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| 6/9/2023 | Kankakee County Speedway - Kankakee, IL Bill Davis Memorial 50 Lap DIRTcar Modified Special DIRTcar UMP Modifieds, DIRTcar Factory Stock, DIRTcar Sport Compact, DIRTcar Pro Modifieds, DIRTcar Stock Car, DIRTcar Pro Late Models | Results | | Jesse Simmons (DIRTcar Stock Car) | 4th | - | - | 7th |
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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 Simmons (Street Stocks) | 4th | - | - | 2nd |
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| 6/15/2023 | Kankakee County Speedway - Kankakee, IL DIRTcar Summer Nationals DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals DIRTcar Factory Stock, Snow - SOO 600, DIRTcar Stock Car, DIRTcar Pro Late Models | Results | | Jesse Simmons (DIRTcar Stock Car) | 3rd | - | - | 5th |
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| 6/16/2023 | Farmer City Raceway - Farmer City, IL Matco Tool Night + Full Show + Pro Mods. Dirt Super Late Models, DIRTcar Late Models, DIRTcar UMP Modifieds, Street Stocks, DIRTcar Pro Modifieds, DIRTcar Pro Late Models | Results | | Jesse Simmons (Street Stocks) | 2nd | - | - | 4th |
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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 Simmons (Street Stocks) | 1st | - | - | 2nd |
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| 6/23/2023 | Kankakee County Speedway - Kankakee, IL DIRTcar Stock Car Special + On Track Autograph Session DIRTcar UMP Modifieds, DIRTcar Factory Stock, DIRTcar Sport Compact, DIRTcar Pro Modifieds, DIRTcar Stock Car, DIRTcar Pro Late Models | Results | | Jesse Simmons (DIRTcar Stock Car) | 3rd | - | - | 5th |
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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 Simmons (Street Stocks) | 4th | - | - | 4th |
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| 6/30/2023 | Kankakee County Speedway - Kankakee, IL DIRTcar Pro Modified Special + Kids Bicycle Decoration Contest + Crown Victorias DIRTcar UMP Modifieds, DIRTcar Factory Stock, DIRTcar Sport Compact, Stock Cars, DIRTcar Pro Modifieds, DIRTcar Stock Car, DIRTcar Pro Late Models | Results | | Jesse Simmons (DIRTcar Stock Car) | 4th | - | - | 6th |
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| 7/7/2023 | Kankakee County Speedway - Kankakee, IL DIRTcar Factory Stock, DIRTcar Sport Compact, Stock Cars, DIRTcar Pro Modifieds, DIRTcar Stock Car, DIRTcar Pro Late Models | Results | | Jesse Simmons (DIRTcar Stock Car) | 3rd | - | - | 6th |
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| 7/8/2023 | Fairbury Speedway - Fairbury, IL FALS Cup Special DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Street Stocks | Results | | Jesse Simmons (DIRTcar UMP Modifieds) | 9th | - | 7th | - | | Jesse Simmons (Street Stocks) | 1st | - | - | 4th |
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| 7/14/2023 | 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 | | Jesse Simmons (Street Stocks) | 2nd | - | - | 4th |
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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 Simmons (DIRTcar UMP Modifieds) | 5th | - | 1st | 12th | | Jesse Simmons (Street Stocks) | 1st | - | - | 1st |
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| 7/19/2023 | Christian County Fair - Taylorville, IL Christian County Fair DIRTcar Sport Compact, Sportsmans, Street Stocks | Results | | Jesse Simmons (Street Stocks) | 5th | - | - | 5th |
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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 | | Jesse Simmons (DIRTcar Stock Car) | 3rd | - | - | 4th |
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| 7/22/2023 | Charleston Speedway - Charleston, IL Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, 600cc Modifieds, DIRTcar Pro Modifieds | Results | | Jesse Simmons (Street Stocks) | 1st | - | - | 2nd |
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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 Simmons (Street Stocks) | 4th | - | - | 4th |
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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 Simmons (Street Stocks) | 1st | - | - | 4th |
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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 | | Jesse Simmons (Street Stocks) | 4th | - | - | 3rd |
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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 Simmons (Street Stocks) | 3rd | - | - | 4th |
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| 8/18/2023 | 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 | | Jesse Simmons (Street Stocks) | 5th | - | - | 7th |
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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 Simmons (Street Stocks) | 2nd | - | - | 3rd |
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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 | | Jesse Simmons (DIRTcar Stock Car) | 2nd | - | - | 1st |
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| 8/26/2023 | Charleston Speedway - Charleston, IL Weekly Championship Racing DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Jesse Simmons (Street Stocks) | 1st | - | - | 2nd |
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| 9/1/2023 | Kankakee County Speedway - Kankakee, IL 50 Lap DIRTcar Pro Late Model Special DIRTcar UMP Modifieds, DIRTcar Factory Stock, DIRTcar Sport Compact, Stock Cars, DIRTcar Pro Modifieds, DIRTcar Stock Car, DIRTcar Pro Late Models | Results | | Jesse Simmons (DIRTcar Stock Car) | 4th | - | - | 8th |
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| 9/2/2023 | Charleston Speedway - Charleston, IL 4th Annual Freaky 40 for Pro Modified presented by McHugh's Double Drive Thru + Add'l Classes DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Jesse Simmons (Street Stocks) | 3rd | - | - | 4th |
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| 9/3/2023 | East Moline Speedway - East Moline, IL Fallon Heros / Ronnie Weedon Memorial Street Stocks, Vintage Full Body Stock Cars, Sport Compact, IMCA Modified, IMCA Northern SportMod | Results | | Jesse Simmons (Street Stocks) | 1st | - | - | 5th |
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| 9/8/2023 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged, 305 Sprints - Winged, DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks | Results | | Jesse Simmons (Street Stocks) | 2nd | - | - | 3rd |
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| 9/9/2023 | Macon Speedway - Macon, IL Ripple's Auto Body night presented by Griz 98.1 FM w/ MOWA Sprint Cars 410 Sprints - Winged: MOWA-Midwest Open Wheel Association DIRTcar UMP Modifieds, DIRTcar Sportsmans, Street Stocks, Mod Lites | Results | | Jesse Simmons (Street Stocks) | 5th | - | - | 7th |
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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 | | Jesse Simmons (DIRTcar Stock Car) | 3rd | - | - | 4th |
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| 9/16/2023 | Charleston Speedway - Charleston, IL Double Down Sizzler for Double Championship Points DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, DIRTcar Pro Modifieds | Results | | Jesse Simmons (Street Stocks) | 3rd | - | - | 2nd |
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| 9/23/2023 | Charleston Speedway - Charleston, IL Championship Night, We Crown Our Champs! DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, 600cc Modifieds, DIRTcar Pro Modifieds | Results | | Jesse Simmons (Street Stocks) | 3rd | - | - | 2nd |
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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 | | Jesse Simmons (DIRTcar Stock Car) | 1st | - | - | 4th |
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| 9/30/2023 | Charleston Speedway - Charleston, IL 2023 DIRTcar Fall Nationals DIRTcar Factory Stock, Street Stocks, Hornets, 600cc Modifieds | Results | | Jesse Simmons (Street Stocks) | 1st | 4th | - | 6th |
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| 10/7/2023 | Charleston Speedway - Charleston, IL Season Finale + Powderpuff & Mechanic Races DIRTcar UMP Modifieds, DIRTcar Factory Stock, Street Stocks, Dirt Late Models, Hornets, Generic 1, Generic 2, DIRTcar Pro Modifieds, Ladies - Bombers, Ladies - Factory Stock | Results | | Jesse Simmons (Street Stocks) | 4th | - | - | 3rd |
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| 10/14/2023 | Kokomo Speedway - Kokomo, IN Kokomo Klash XVII Dirt Super Late Models, A Modifieds, Street Stocks, Hornets | Postponed |
| 10/15/2023 | Kokomo Speedway - Kokomo, IN Kokomo Klash XVII **Rain Date** Dirt Super Late Models, DIRTcar UMP Modifieds, Street Stocks, Hornets | Results | | Jesse Simmons (Street Stocks) | 2nd | - | - | 8th |
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