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| 5/4/2019 | Plymouth Speedway - Plymouth, IN Cabin Fever DIRTcar UMP Modifieds, Super Sports, Stock Non-Wing, Street Stocks, Winged Crate Sprints | Results | | Jesse Simmons (Super Sports) | - | - | - | - | | Jesse Simmons (Street Stocks) | 1st | - | - | 12th |
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| 5/18/2019 | Charleston Speedway - Charleston, IL Regular Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Hornets, Economy Late Models | Results | | Jesse Simmons (DIRTcar Factory Stock) | 1st | - | - | 2nd |
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| 5/25/2019 | Charleston Speedway - Charleston, IL B Mod Special $550 to win $80 to start. DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets | Results | | Jesse Simmons (DIRTcar Factory Stock) | 1st | - | - | DNS |
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| 6/1/2019 | Charleston Speedway - Charleston, IL Regular Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Hornets, Economy Late Models | Results | | Jesse Simmons (DIRTcar Factory Stock) | 2nd | - | - | 2nd |
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| 6/8/2019 | Charleston Speedway - Charleston, IL Regular Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets | Results | | Jesse Simmons (DIRTcar Factory Stock) | 1st | - | - | 1st |
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| 6/29/2019 | Charleston Speedway - Charleston, IL Regular Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Hornets, Economy Late Models | Results | | Jesse Simmons (DIRTcar Factory Stock) | 1st | - | - | 1st |
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| 7/12/2019 | Plymouth Speedway - Plymouth, IN ILVDIRT Stock Car Throwdown at the Playground Night 1 Asphalt Mini Stocks, Super Sports, Stock Non-Wing, Street Stocks | Results | | Jesse Simmons (Street Stocks) | 2nd | - | - | 1st |
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| 7/13/2019 | Charleston Speedway - Charleston, IL Neal Tire $700 to Win $125 to start A-Mod Special DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets | Results | | Jesse Simmons (DIRTcar Factory Stock) | 1st | - | - | 1st |
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| 7/20/2019 | Charleston Speedway - Charleston, IL Regular Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Hornets, Economy Late Models | Results | | Jesse Simmons (DIRTcar Factory Stock) | 1st | - | - | 1st |
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| 7/27/2019 | Charleston Speedway - Charleston, IL Regular Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets | Results | | Jesse Simmons (DIRTcar Factory Stock) | 1st | - | - | 1st |
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| 8/3/2019 | Charleston Speedway - Charleston, IL Regular Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets, Economy Late Models | Results | | Jesse Simmons (DIRTcar Factory Stock) | 1st | - | - | 1st |
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| 8/10/2019 | Charleston Speedway - Charleston, IL Autograph Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets | Results | | Jesse Simmons (DIRTcar Factory Stock) | 4th | - | - | 3rd |
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| 8/17/2019 | Charleston Speedway - Charleston, IL Regular Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Hornets, Economy Late Models | Results | | Jesse Simmons (DIRTcar Factory Stock) | 1st | - | - | 1st |
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| 8/24/2019 | Charleston Speedway - Charleston, IL Regular Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets | Results | | Jesse Simmons (DIRTcar Factory Stock) | 2nd | - | - | 1st |
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| 8/31/2019 | Charleston Speedway - Charleston, IL Hornet Special DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Hornets, Economy Late Models | Results | | Jesse Simmons (DIRTcar Factory Stock) | 2nd | - | - | 3rd |
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| 9/7/2019 | Charleston Speedway - Charleston, IL Regular Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets | Results | | Jesse Simmons (DIRTcar Factory Stock) | 1st | - | - | 2nd |
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| 9/14/2019 | Charleston Speedway - Charleston, IL Freaky 40 For Bmods DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Hornets, Economy Late Models, 600cc Modifieds | Results | | Jesse Simmons (DIRTcar Factory Stock) | 1st | - | - | 1st |
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| 9/21/2019 | Charleston Speedway - Charleston, IL Double Points Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Hornets, Economy Late Models, 600cc Modifieds | Results | | Jesse Simmons (DIRTcar Factory Stock) | 3rd | - | - | 2nd |
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| 9/28/2019 | Charleston Speedway - Charleston, IL Regular Night DIRTcar UMP Modifieds, DIRTcar Factory Stock, B Modifieds, Street Stocks, Hornets | Results | | Jesse Simmons (DIRTcar Factory Stock) | 1st | - | - | 1st |
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| 10/5/2019 | Charleston Speedway - Charleston, IL Sixth Annual DIRTcar Stock Car Fall Nationals Street Stocks: Midwest Stock Car Tour DIRTcar Factory Stock, B Modifieds, Hornets | Results | | Jesse Simmons (DIRTcar Factory Stock) | 1st | - | - | DNS | | Jesse Simmons (Street Stocks) | 5th | - | 4th (DNF) | - |
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| 10/19/2019 | Kokomo Speedway - Kokomo, IN Kokomo Klash XIII A Modifieds, Street Stocks, Dirt Late Models, Hornets, Super Stocks | Results | | Jesse Simmons (Street Stocks) | 5th | - | 1st | 16th |
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