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| 5/1/2021 | US 24 Speedway - Logansport, IN Great 8 weekly $500 to win any class 20 + cars point night 1 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Stock Non-Wing, Junior Sprints, Senior Micros | Results | | Will Bennett (Stock Non-Wing) | 8th | - | DNS | - |
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| 5/22/2021 | US 24 Speedway - Logansport, IN Weekly Rest NW point night #2 GREAT 8 Winged Outlaw, Non-Wing Outlaw, Restricted Non Winged Micros, Winged A-Class, Stock Non-Wing, Junior Sprints, Senior Micros | Results | | Will Bennett (Stock Non-Wing) | 6th | - | 2nd | - |
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| 5/26/2021 | Miami County Raceway - Peru, IN Performance Electronics "Bring the Wing" & Open Practice Winged Outlaw, Hybrid 600cc Micros | Results | | Will Bennett (Hybrid 600cc Micros) | - | - | - | - |
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| 5/27/2021 | Miami County Raceway - Peru, IN PE3 Non-Wing World Championship Hybrid 600cc Micros | Results | | Will Bennett (Hybrid 600cc Micros) | 7th | - | 13th | - |
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| 5/28/2021 | Miami County Raceway - Peru, IN PE3 Non-Wing World Championship Hybrid 600cc Micros | Results | | Will Bennett (Hybrid 600cc Micros) | 2nd | - | 9th | - |
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| 5/29/2021 | Miami County Raceway - Peru, IN PE3 Non-Wing World Championship Hybrid 600cc Micros | Results | | Will Bennett (Hybrid 600cc Micros) | 6th | - | - | - |
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| 6/26/2021 | Circle City Raceway - Indianapolis, IN Marion County Fair-Summit American Modified Series, Speedrome Stocks & FFWD, Fords, All Star TQ's DIRTcar UMP Modifieds: Summit American Modified Series TQ Midgets: All Star TQ Midgets Stock Cars, Hornets, Crown Vic | Results | | Will Bennett (DIRTcar UMP Modifieds) | 3rd | - | - | 18th |
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| 7/4/2021 | Circle City Raceway - Indianapolis, IN Marion County Fair -Summit American Modified Series, Indiana Superstocks, PLUS FORDS, HORNETS/FFWD DIRTcar UMP Modifieds: Summit American Modified Series Stock Cars, Hornets, Crown Vic | Results | | Will Bennett (DIRTcar UMP Modifieds) | 5th | - | - | 17th |
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| 7/17/2021 | Lincoln Park Speedway - Putnamville, IN Saturday Night Racing DIRTcar UMP Modifieds, Factory Stocks, 410 Sprints - Non-Winged, Super Stocks | Results | | Will Bennett (DIRTcar UMP Modifieds) | 4th | - | - | 5th |
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| 7/24/2021 | Lincoln Park Speedway - Putnamville, IN Baily Hicks Memorial Lightning Sprints: Midwest Mini Sprint Association 305 Sprints - Winged, DIRTcar UMP Modifieds, Factory Stocks, Hornets, Super Stocks | Results | | Will Bennett (DIRTcar UMP Modifieds) | 2nd | - | - | DNS |
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| 8/7/2021 | Lincoln Park Speedway - Putnamville, IN Saturday Night Racing DIRTcar UMP Modifieds, Factory Stocks, 410 Sprints - Non-Winged, Hornets, Super Stocks | Results | | Will Bennett (DIRTcar UMP Modifieds) | 6th | - | - | DNS |
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| 8/28/2021 | Lincoln Park Speedway - Putnamville, IN Buckeye Bob 33 - Gary Rickets Memorial DIRTcar UMP Modifieds, Factory Stocks, 410 Sprints - Non-Winged, Super Stocks | Results | | Will Bennett (DIRTcar UMP Modifieds) | 1st | - | - | 2nd |
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| 9/4/2021 | Fairbury Speedway - Fairbury, IL $10,000 to win $500 to start DIRTcar UMP Modifieds: Summit American Modified Series DIRTcar Late Models | Results | | Will Bennett (DIRTcar UMP Modifieds) | 5th | - | 3rd | 19th (DNF) |
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| 9/5/2021 | Circle City Raceway - Indianapolis, IN Crate Late Models, UMP Modifieds, Steel Block Sprint Cars, Fords, Legends DIRTcar UMP Modifieds, 410 Sprints - Non-Winged, Pro Legends, Dirt Crate Late Models, Crown Vic | Results | | Will Bennett (DIRTcar UMP Modifieds) | 3rd | - | - | 5th |
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| 9/18/2021 | Lincoln Park Speedway - Putnamville, IN Saturday Night Racing 305 Sprints - Winged, DIRTcar UMP Modifieds, Factory Stocks, 410 Sprints - Non-Winged, Super Stocks | Rain Out |
| 9/25/2021 | Lincoln Park Speedway - Putnamville, IN Rescheduled King of Nonwing and Fireworks DIRTcar UMP Modifieds, Factory Stocks, 410 Sprints - Non-Winged, Super Stocks | Results | | Will Bennett (DIRTcar UMP Modifieds) | 2nd | - | - | 4th |
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| 10/9/2021 | Fairbury Speedway - Fairbury, IL FALS Frenzy DIRTcar Late Models, DIRTcar UMP Modifieds, Pro Late Model | Results | | Will Bennett (DIRTcar UMP Modifieds) | 4th | - | 1st | 16th (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 | | Will Bennett (A Modifieds) | - | - | - | - |
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