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| 4/8/2023 | Charleston Speedway - Charleston, IL 2nd ANNUAL CAR SHOW +PLUS+ OPEN Test-Tune ALL Classes/ALL Divisions/ALL Race Cars Are Welcome! Midgets, DIRTcar UMP Modifieds, DIRTcar Factory Stock, Winged Outlaw, Street Stocks, Dirt Late Models, 410 Sprints - Non-Winged, Non-Winged Sprints, Hornets, Economy Late Models, 600cc Modifieds, Pro Late Model, DIRTcar Pro Modifieds | Results | | Matt Dillon (DIRTcar UMP Modifieds) | - | - | - | - |
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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 | | Matt Dillon (DIRTcar UMP Modifieds) | 1st | - | - | 3rd |
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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 | | Matt Dillon (DIRTcar UMP Modifieds) | 3rd | - | - | 3rd |
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| 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 | | Matt Dillon (DIRTcar UMP Modifieds) | 6th | - | 14th | - |
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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 | | Matt Dillon (DIRTcar UMP Modifieds) | 5th | - | - | 8th |
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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 | | Matt Dillon (DIRTcar UMP Modifieds) | 4th | - | - | 9th |
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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 | | Matt Dillon (DIRTcar UMP Modifieds) | 4th | - | - | 8th |
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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 | | Matt Dillon (DIRTcar UMP Modifieds) | 3rd | - | - | 16th |
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| 6/22/2023 | Charleston Speedway - Charleston, IL The Tenth Annual POWRi Illinois SPEEDweek Opener Midgets: POWRi National Midgets with POWRi DIRTcar UMP Modifieds, Hornets, DIRTcar Pro Modifieds | Results | | Matt Dillon (DIRTcar UMP Modifieds) | 4th | - | - | 3rd |
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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 | | Matt Dillon (DIRTcar UMP Modifieds) | 8th | - | - | 9th |
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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 | | Matt Dillon (DIRTcar UMP Modifieds) | 5th | - | 1st | 7th |
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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 | | Matt Dillon (DIRTcar UMP Modifieds) | 2nd | - | - | 6th |
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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 | | Matt Dillon (DIRTcar UMP Modifieds) | 5th | - | - | 10th |
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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 | | Matt Dillon (DIRTcar UMP Modifieds) | DNS | - | 5th | 15th |
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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 | | Matt Dillon (DIRTcar UMP Modifieds) | 3rd | - | - | 7th |
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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 | | Matt Dillon (DIRTcar UMP Modifieds) | 5th | - | - | 13th |
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| 9/1/2023 | 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 DIRTcar UMP Modifieds, Street Stocks, DIRTcar Pro Late Models | Results | | Matt Dillon (DIRTcar UMP Modifieds) | 8th | - | 6th | - |
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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 | | Matt Dillon (DIRTcar UMP Modifieds) | 3rd | - | - | 6th |
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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 | | Matt Dillon (DIRTcar UMP Modifieds) | 4th | - | - | 7th |
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| 9/30/2023 | Lincoln Speedway - Lincoln, IL DIRTcar Fall Nationals Night 2 DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Pro Modifieds, DIRTcar Pro Late Models | Results | | Matt Dillon (DIRTcar UMP Modifieds) | 9th | - | 7th | - |
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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 | | Matt Dillon (DIRTcar UMP Modifieds) | 2nd | - | - | 17th |
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