| | Heat | Dash | B Feature | A Feature |
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| 1/1/2021 | Tulsa Expo Raceway - Tulsa, OK Racing Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Chad Winfrey (Stock Non-Wing) | - | - | - | - |
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| 1/14/2021 | Tulsa Expo Raceway - Tulsa, OK John Christner Trucking Qualifying Night Midgets: Chili Bowl Nationals | Results | | Chad Winfrey (Midgets) | 3rd | 7th | 8th | - |
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| 1/16/2021 | Tulsa Expo Raceway - Tulsa, OK Lucas Oil Championship Feature Events Midgets: Chili Bowl Nationals | Results | | Chad Winfrey (Midgets) | - | - | - | - |
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| 5/7/2021 | KC Raceway - Independence, MO Micros Midgets: POWRi Central States Midgets Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Chad Winfrey (Midgets) | 4th | - | - | 2nd |
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| 6/5/2021 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race (6) Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Chad Winfrey (Stock Non-Wing) | 3rd | - | - | 12th (DNF) |
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| 6/11/2021 | Electric City Speedway - Butler, MO Factory Stocks, Midwest Modifieds, Street Stocks, Non-Winged Sprints, Sport Compact, USRA B-Mods, USRA Modifieds | Results | | Chad Winfrey (Midgets) | - | - | - | 4th | | Chad Winfrey (Non-Winged Sprints) | 4th | - | - | 4th |
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| 6/12/2021 | Valley Speedway - Grain Valley, MO O'Reilly's Auto Parts Points Race Night Midgets: POWRi Central States Midgets Hobby Stocks, Midwest Modifieds, IMCA Northern SportMod, IMCA Stock Car, Mod Lites | Results | | Chad Winfrey (Midgets) | 2nd | - | - | 1st |
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| 7/17/2021 | Valley Speedway - Grain Valley, MO Thunder in the Valley National Powri Midgets/Powri WAR Sprints series Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Non-Winged Sprints: POWRi WAR Sprints Sportsman Sprints | Results | | Chad Winfrey (Midgets) | 5th | - | - | 23rd |
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| 7/18/2021 | Sweet Springs Motorsports Complex - Sweet Springs, MO Thunder in the Valley Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Non-Wing Outlaw, Senior Micros | Results | | Chad Winfrey (Midgets) | 8th | - | 4th | 20th |
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| 8/14/2021 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race (16) Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Chad Winfrey (Stock Non-Wing) | 1st | - | - | 1st |
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| 9/4/2021 | I-35 Speedway - Winston, MO DSF Flooring Night - USAC Midwest Wingless Sprints & Bill Lawson Memorial - Outlaw Midgets Special Midgets: POWRi Central States Midgets Non-Winged Sprints: Midwest Wingless Racing Association Hobby Stocks, Midwest Modifieds, Dirt Late Models, Sport Compact, USRA B-Mods, USRA Modifieds, USRA Stock Cars | Results | | Chad Winfrey (Midgets) | 3rd | - | - | 3rd |
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| 9/11/2021 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race (20) Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Chad Winfrey (Stock Non-Wing) | 8th (DNF) | - | - | 13th (DNF) |
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| 9/25/2021 | Valley Speedway - Grain Valley, MO MWRA and Valley Speedway classes final points championship Midgets: POWRi Central States Midgets Non-Winged Sprints: Midwest Wingless Racing Association Hobby Stocks, Midwest Modifieds, Economy Sprints - Non Winged, Mod Lites | Results | | Chad Winfrey (Midgets) | 2nd | - | - | 2nd |
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| 10/1/2021 | Sweet Springs Motorsports Complex - Sweet Springs, MO Sweet Springs Fall Brawl Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw, Restricted 'A' Class, Stock Non-Wing, Junior Sprints | Results | | Chad Winfrey (Midgets) | 6th | - | 4th | 19th |
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| 10/2/2021 | Sweet Springs Motorsports Complex - Sweet Springs, MO Sweet Springs Fall Brawl Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw, Restricted 'A' Class, Stock Non-Wing, Junior Sprints | Results | | Chad Winfrey (Midgets) | 8th | - | - | 12th |
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| 12/28/2021 | Tulsa Expo Raceway - Tulsa, OK PM: Practice Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Chad Winfrey (Non-Wing Outlaw) | - | - | - | - | | Chad Winfrey (Stock Non-Wing) | - | - | - | - |
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| 12/29/2021 | Tulsa Expo Raceway - Tulsa, OK Races Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class | Results | | Chad Winfrey (Non-Wing Outlaw) | 6th | - | - | - |
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| 12/30/2021 | Tulsa Expo Raceway - Tulsa, OK Races Non-Wing Outlaw, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Chad Winfrey (Non-Wing Outlaw) | - | - | - | - | | Chad Winfrey (Stock Non-Wing) | 3rd | - | - | - |
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| 12/31/2021 | Tulsa Expo Raceway - Tulsa, OK Races Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Chad Winfrey (Stock Non-Wing) | - | - | - | - |
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