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| 1/1/2020 | Tulsa Expo Raceway - Tulsa, OK Morning Practice / Evening Races Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Chad Winfrey (Non-Wing Outlaw) | 1st | - | - | - | | Chad Winfrey (Stock Non-Wing) | - | - | - | - |
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| 1/2/2020 | Tulsa Expo Raceway - Tulsa, OK Races Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Chad Winfrey (Non-Wing Outlaw) | - | - | - | - | | Chad Winfrey (Stock Non-Wing) | 3rd | - | - | - |
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| 1/3/2020 | Tulsa Expo Raceway - Tulsa, OK Races Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Chad Winfrey (Non-Wing Outlaw) | - | 8th | - | - | | Chad Winfrey (Stock Non-Wing) | - | - | - | - |
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| 1/4/2020 | Tulsa Expo Raceway - Tulsa, OK #WintheDriller Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Chad Winfrey (Non-Wing Outlaw) | - | - | 6th | - | | Chad Winfrey (Stock Non-Wing) | - | - | 8th | - |
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| 1/16/2020 | Tulsa Expo Raceway - Tulsa, OK John Christner Trucking Qualifying Night Midgets: Chili Bowl Nationals | Results | | Chad Winfrey (Midgets) | 4th | 8th | 10th | - |
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| 1/18/2020 | Tulsa Expo Raceway - Tulsa, OK Lucas Oil Championship Night Midgets: Chili Bowl Nationals | Results | | Chad Winfrey (Midgets) | - | - | - | - |
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| 5/16/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Chad Winfrey (Non-Wing Outlaw) | 7th | - | - | 9th | | Chad Winfrey (Stock Non-Wing) | 1st | - | - | 19th (DNF) |
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| 5/23/2020 | Valley Speedway - Grain Valley, MO Powri Mid-State Open Wheel Nationals Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Non-Winged Sprints: POWRi WAR Sprints | Results | | Chad Winfrey (Midgets) | 6th | - | 1st | 13th |
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| 5/24/2020 | Valley Speedway - Grain Valley, MO Mid-State Open Wheel Nationals Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Non-Winged Sprints: POWRi WAR Sprints | Results | | Chad Winfrey (Midgets) | 6th | - | 14th | - |
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| 5/30/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Chad Winfrey (Stock Non-Wing) | 3rd | - | - | 25th (DNF) |
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| 6/6/2020 | Valley Speedway - Grain Valley, MO Valley Speedway points series Midgets: POWRi Non-Winged Sprints: POWRi WAR Sprints Sportsman Sprints, Factory Stocks, Hobby Stocks, Midwest Modifieds, B Modifieds | Results | | Chad Winfrey (Midgets) | 1st | - | - | 2nd |
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| 6/13/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Chad Winfrey (Stock Non-Wing) | 1st | - | - | 5th |
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| 7/11/2020 | Valley Speedway - Grain Valley, MO Powri National Midgets, Powri Micro Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw | Results | | Chad Winfrey (Midgets) | 6th | - | 5th | - |
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| 7/12/2020 | Valley Speedway - Grain Valley, MO Powri National Midgets, Powri Micro, Lightning Sprints Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw | Results | | Chad Winfrey (Midgets) | 6th | - | 14th | - |
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| 8/1/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO 25th Anniversary Jr. Sprint National Show and Weekly Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Chad Winfrey (Stock Non-Wing) | 2nd | - | - | 8th |
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| 8/8/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Chad Winfrey (Stock Non-Wing) | 7th (DNF) | - | - | 21st (DNF) |
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| 8/22/2020 | Valley Speedway - Grain Valley, MO Valley Speedway points race Midgets, Factory Stocks, Hobby Stocks, Midwest Modifieds, B Modifieds, 250cc+ Open Quad, Quad A Class | Results | | Chad Winfrey (Midgets) | 1st | - | - | 1st |
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| 9/4/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO USAC National Midgets and Winged Outlaw Micros Midgets | Results | | Chad Winfrey (Midgets) | 6th | - | 9th | - |
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| 9/5/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO USAC National Midgets and Winged Outlaw Micros Midgets | Results | | Chad Winfrey (Midgets) | 7th | - | 11th | - |
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| 9/19/2020 | Valley Speedway - Grain Valley, MO Valley Speedway points race Midgets, Factory Stocks, Hobby Stocks, Midwest Modifieds, B Modifieds, 250cc+ Open Quad, Quad A Class | Results | | Chad Winfrey (Midgets) | 1st | - | - | 2nd |
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| 9/26/2020 | Valley Speedway - Grain Valley, MO Colonel John Helm Memorial points championship finals Midgets: POWRi Non-Winged Sprints: POWRi WAR Sprints Factory Stocks, Hobby Stocks, Midwest Modifieds, B Modifieds, Economy Sprints - Non Winged, 250cc+ Open Quad, Quad A Class | Results | | Chad Winfrey (Midgets) | 2nd | - | - | 3rd |
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| 12/28/2020 | Tulsa Expo Raceway - Tulsa, OK AM: Early Move-In / PM: Regular Move-In Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Chad Winfrey (Non-Wing Outlaw) | - | - | - | - | | Chad Winfrey (Stock Non-Wing) | - | - | - | - |
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| 12/30/2020 | Tulsa Expo Raceway - Tulsa, OK Racing Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, 600cc Modifieds | Results | | Chad Winfrey (Non-Wing Outlaw) | 6th | - | - | - |
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| 12/31/2020 | Tulsa Expo Raceway - Tulsa, OK Racing Winged Outlaw, Non-Wing Outlaw, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Chad Winfrey (Non-Wing Outlaw) | - | - | - | - | | Chad Winfrey (Stock Non-Wing) | 4th | - | - | - |
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