| | Heat | Dash | B Feature | A Feature |
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| 4/17/2021 | Highland Speedway - Highland, IL DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Dustin Clary (Winged Outlaw) | 2nd | - | - | 16th |
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| 5/1/2021 | Highland Speedway - Highland, IL DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Dustin Clary (Winged Outlaw) | 6th | - | - | 6th |
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| 5/7/2021 | Coles County Speedway - Mattoon, IL Weekly Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Dustin Clary (Winged Outlaw) | 2nd | - | - | 1st |
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| 6/5/2021 | Southern Illinois Raceway - Marion, IL Performance Electronics Prelude to the Hustle Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Dustin Clary (Winged Outlaw) | 7th | - | 7th (DNF) | - |
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| 6/26/2021 | Farmington Empire Speedway - Farmington, MO $3,000-to-win 410 c.i. Sprints 410 Sprints - Winged | Results | | Dustin Clary (410 Sprints - Winged) | 4th | - | - | 11th |
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| 7/30/2021 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association | Results | | Dustin Clary (410 Sprints - Winged) | 5th | - | - | 19th |
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| 8/20/2021 | Charleston Speedway - Charleston, IL POWRi at Charleston Speedway Midgets: POWRi National Midgets with POWRi Winged Outlaw, Hornets, DIRTcar Pro Modifieds | Results | | Dustin Clary (Winged Outlaw) | 4th | - | - | 13th |
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| 8/27/2021 | Tri City Speedway - Granite City, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact | Results | | Dustin Clary (410 Sprints - Winged) | 6th | - | - | 12th |
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| 9/10/2021 | Jacksonville Speedway - Jacksonville, IL Herb Barlow Memorial 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Dustin Clary (410 Sprints - Winged) | 7th | - | 7th | - |
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| 9/17/2021 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged, 305 Sprints - Winged | Results | | Dustin Clary (410 Sprints - Winged) | - | - | - | DNS |
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| 9/24/2021 | Jacksonville Speedway - Jacksonville, IL | Results | | Dustin Clary (410 Sprints - Winged) | 4th | - | - | 12th (DNF) |
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| 9/25/2021 | Farmington Empire Speedway - Farmington, MO Weekly 410 Racing 410 Sprints - Winged | Results | | Dustin Clary (410 Sprints - Winged) | 7th | - | - | 10th |
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