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| 7/18/2020 | Macon Speedway - Macon, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Cliff Powell (Winged A-Class) | 6th | - | - | 12th (DNF) |
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| 8/7/2020 | Coles County Speedway - Mattoon, IL HART Series Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Cliff Powell (Winged Outlaw) | DNS | - | - | 6th | | Cliff Powell (Non-Wing Outlaw) | 3rd | - | - | 16th (DNF) |
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| 8/15/2020 | Macon Speedway - Macon, IL Eve of Destruction VI with FIREWORKS & Diane Bennett Memorial DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Cliff Powell (Winged A-Class) | 9th (DNF) | - | - | 13th |
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| 8/23/2020 | Jacksonville Speedway - Jacksonville, IL POWRi Midgets and Micros at Jacksonville Speedway Midgets: POWRi Winged Outlaw | Results | | Cliff Powell (Winged Outlaw) | 7th | - | 5th | 20th |
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| 9/4/2020 | Tri City Speedway - Granite City, IL "Test Drive Technologies Night" LM/Mod/BMod/St.Stock/4-Cyl/Winged Micros plus Kids Power Wheels DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Winged Outlaw, B Modifieds, Street Stocks | Results | | Cliff Powell (Winged Outlaw) | 6th | - | - | 9th |
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| 9/5/2020 | Macon Speedway - Macon, IL Regular Night of Weekly Racing DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Cliff Powell (Winged A-Class) | 4th | - | - | 6th |
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| 9/11/2020 | Jacksonville Speedway - Jacksonville, IL Herb Barlow Memorial 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi Winged Outlaw | Results | | Cliff Powell (Winged Outlaw) | - | - | - | - |
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| 9/13/2020 | Tri City Speedway - Granite City, IL "Sunday Funday" Mods $700/BMods $500/St. Stocks $300/4-cyl $200/Non-Winged Micros $300 DIRTcar UMP Modifieds, DIRTcar Sport Compact, Non-Wing Outlaw, B Modifieds, Street Stocks | Results | | Cliff Powell (Non-Wing Outlaw) | 3rd | - | - | 4th |
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| 9/19/2020 | 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 | | Cliff Powell (Non-Wing Outlaw) | 4th | - | - | 18th |
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| 9/20/2020 | Tri City Speedway - Granite City, IL "Sunday Funday" Mods $700/BMods $500/St. Stocks $300/4-cyl $200/Non-Winged Micros $300 DIRTcar UMP Modifieds, DIRTcar Sport Compact, Non-Wing Outlaw, B Modifieds, Street Stocks | Results | | Cliff Powell (Non-Wing Outlaw) | 3rd | - | - | 2nd |
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| 9/26/2020 | Macon Speedway - Macon, IL Season Championship "Racing for Cup" and Give Back to the fans DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Cliff Powell (Winged A-Class) | 6th | - | - | 8th |
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| 10/2/2020 | Tri City Speedway - Granite City, IL POWRI Midgets/MOWA Sprint /305 Sprints/HART Non-Winged Micros 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi 305 Sprints - Winged, Non-Wing Outlaw | Results | | Cliff Powell (Non-Wing Outlaw) | 5th | - | - | 9th |
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| 10/9/2020 | Jacksonville Speedway - Jacksonville, IL Ron Milton Race of Champions Midgets: POWRi 410 Sprints - Winged, Winged Outlaw | Results | | Cliff Powell (Winged Outlaw) | 6th | - | 10th | - |
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| 10/17/2020 | Wayne County Speedway - Wayne City, IL Gateway Vintage Racers Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Cliff Powell (Non-Wing Outlaw) | 8th (DNF) | - | - | 12th | | Cliff Powell (Stock Non-Wing) | 4th | - | - | 6th |
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| 11/7/2020 | Wayne County Speedway - Wayne City, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Cliff Powell (Winged Outlaw) | 7th | - | - | 9th | | Cliff Powell (Non-Wing Outlaw) | 6th | - | 4th | - |
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| 11/13/2020 | KC Raceway - Independence, MO MICRO/Points Race 16 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Mod Lites | Results | | Cliff Powell (Winged Outlaw) | 5th | - | - | 8th | | Cliff Powell (Non-Wing Outlaw) | - | - | - | - | | Cliff Powell (Stock Non-Wing) | 3rd | - | - | 4th |
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| 11/20/2020 | Wayne County Speedway - Wayne City, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Cliff Powell (Winged Outlaw) | 5th | - | - | 9th | | Cliff Powell (Non-Wing Outlaw) | 7th | - | - | 11th |
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| 11/29/2020 | Wayne County Speedway - Wayne City, IL Sunday Special Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Cliff Powell (Winged Outlaw) | 4th | - | - | 8th | | Cliff Powell (Non-Wing Outlaw) | 5th | - | - | 10th |
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