| | 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 | | Chad Elliott (Winged Outlaw) | 1st | - | - | 18th |
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| 5/1/2021 | Highland Speedway - Highland, IL DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Chad Elliott (Winged Outlaw) | 7th | - | - | 8th |
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| 5/8/2021 | Macon Speedway - Macon, IL Midwest Season Opener Midgets: POWRi National Midgets with POWRi DIRTcar UMP Modifieds, Winged Outlaw, Hornets, Pro Late Model | Rain Out |
| 5/15/2021 | Highland Speedway - Highland, IL DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Chad Elliott (Winged Outlaw) | 1st | - | - | 11th |
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| 5/21/2021 | Charleston Speedway - Charleston, IL ILLIANA Showdown Midgets: POWRi National Midgets with POWRi Non-Winged Sprints: POWRi WAR Sprints Winged Outlaw | Results | | Chad Elliott (Winged Outlaw) | 7th | - | - | 16th |
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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 | | Chad Elliott (Winged Outlaw) | 9th (DNF) | - | 4th | - |
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| 6/18/2021 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Chad Elliott (Winged Outlaw) | 3rd | - | - | 8th |
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| 7/2/2021 | Sweet Springs Motorsports Complex - Sweet Springs, MO Small Town Throwdown Winged Outlaw | Results | | Chad Elliott (Winged Outlaw) | 7th | - | 13th (DNF) | - |
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| 7/3/2021 | Sweet Springs Motorsports Complex - Sweet Springs, MO Small Town Throwdown Championship Night Winged Outlaw | Results | | Chad Elliott (Winged Outlaw) | 6th | - | DNS | - |
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| 8/7/2021 | Wayne County Speedway - Wayne City, IL Hyper NON-Wing Outlaws $1250 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Chad Elliott (Winged Outlaw) | 8th | - | 3rd | 12th |
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