| | Heat | Dash | B Feature | A Feature |
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| 5/30/2020 | Charleston Speedway - Charleston, IL Opening Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets | Results | | Jesse Simmons (DIRTcar Factory Stock) | 1st | - | - | 3rd |
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| 5/30/2020 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Asphalt Mini Stocks, Super Sports, Stock Non-Wing, Street Stocks | Results | | Jesse Simmons (Street Stocks) | - | - | - | - |
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| 6/6/2020 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Asphalt Mini Stocks, Super Sports, Stock Non-Wing, Street Stocks | Results | | Jesse Simmons (Street Stocks) | 5th | - | - | 4th |
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| 6/13/2020 | Charleston Speedway - Charleston, IL DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets | Results | | Jesse Simmons (DIRTcar Factory Stock) | 3rd | - | - | 3rd |
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| 6/20/2020 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Asphalt Mini Stocks, Super Sports, Stock Non-Wing, Street Stocks | Results | | Jesse Simmons (Street Stocks) | 2nd | - | - | 3rd |
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| 6/27/2020 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Super Sports, Street Stocks | Results | | Jesse Simmons (Street Stocks) | 1st | - | - | 2nd |
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| 7/11/2020 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Asphalt Mini Stocks, Stock Non-Wing, Street Stocks | Results | | Jesse Simmons (Street Stocks) | 5th | - | - | 7th |
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| 7/25/2020 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Super Sports, Stock Non-Wing, Street Stocks | Results | | Jesse Simmons (Street Stocks) | 7th | - | - | 19th |
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| 8/8/2020 | Charleston Speedway - Charleston, IL Driver Autograph Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets, Economy Late Models | Results | | Jesse Simmons (DIRTcar Factory Stock) | 2nd | - | - | 3rd |
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| 8/15/2020 | Charleston Speedway - Charleston, IL DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets | Results | | Jesse Simmons (DIRTcar Factory Stock) | 2nd | - | - | 12th (DNF) |
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| 8/29/2020 | Charleston Speedway - Charleston, IL DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets | Results | | Jesse Simmons (DIRTcar Factory Stock) | 3rd | - | - | 2nd |
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| 9/19/2020 | Charleston Speedway - Charleston, IL Double Points Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets, Economy Late Models | Results | | Jesse Simmons (DIRTcar Factory Stock) | 1st | - | - | 2nd |
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| 9/26/2020 | Charleston Speedway - Charleston, IL The Jim Campbell Memorial - Last Night For Points DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets | Results | | Jesse Simmons (DIRTcar Factory Stock) | 2nd | - | - | 3rd |
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| 10/3/2020 | Charleston Speedway - Charleston, IL Stock Car and Factory Stock Fall Nationals DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets, Economy Late Models | Results | | Jesse Simmons (DIRTcar Factory Stock) | 4th | - | - | 5th | | Jesse Simmons (Street Stocks) | - | - | - | - |
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| 10/10/2020 | Charleston Speedway - Charleston, IL Powder Puff & Mechanics Race DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets, 600cc Modifieds | Results | | Jesse Simmons (DIRTcar Factory Stock) | DNS | - | - | 15th | | Jesse Simmons (B Modifieds) | 4th (DNF) | - | - | 3rd |
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| 10/16/2020 | Kokomo Speedway - Kokomo, IN Kokomo KlashXIV 305 Sprints - Winged, Midgets, Hobby Stocks, 410 Sprints - Non-Winged | Results | | Jesse Simmons (Hobby Stocks) | - | - | - | - |
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| 10/17/2020 | Kokomo Speedway - Kokomo, IN Kokomo KlashXIV Dirt Super Late Models, Hobby Stocks, A Modifieds, Street Stocks, Hornets, Super Stocks | Results | | Jesse Simmons (Street Stocks) | - | - | - | - |
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