| | Heat | Dash | B Feature | A Feature |
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| 4/21/2023 | Jacksonville Speedway - Jacksonville, IL Opening Night 410 Sprints - Winged, 305 Sprints - Winged, DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks | Results | | Cliff Powell (Winged Outlaw) | 5th | - | - | 8th |
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| 4/28/2023 | Tri City Speedway - Granite City, IL 410 Sprints - Winged: World of Outlaws HART Non-Wing Micros | Results | | Cliff Powell (HART Non-Wing Micros) | 5th | - | - | 13th |
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| 4/29/2023 | Macon Speedway - Macon, IL $1 Dogs / $2 Beers / Vintage Racing of Illinois DIRTcar UMP Modifieds, B Modifieds, Vintage Full Body Stock Cars, Hornets, Pro Late Model, HART Non-Wing Micros | Results | | Cliff Powell (HART Non-Wing Micros) | 9th | - | - | 9th |
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| 5/5/2023 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association 305 Sprints - Winged, DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks | Results | | Cliff Powell (Winged Outlaw) | 8th | - | - | 14th |
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| 5/12/2023 | Jacksonville Speedway - Jacksonville, IL $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions 305 Sprints - Winged, Winged Outlaw | Results | | Cliff Powell (Winged Outlaw) | 7th | - | - | 10th |
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| 5/31/2023 | Tri City Speedway - Granite City, IL 410 Sprints - Winged: Kubota High Limit Racing HART Non-Wing Micros | Results | | Cliff Powell (HART Non-Wing Micros) | 5th | - | - | 11th |
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| 6/1/2023 | Tri City Speedway - Granite City, IL Xtreme Outlaw Midgets Midgets: Xtreme Outlaw Midgets DIRTcar UMP Modifieds, Junior Sprints, Restricted Box Stock, HART Non-Wing Micros, LO 206 Cage Junior 1 Winged | Results | | Cliff Powell (HART Non-Wing Micros) | 7th | - | - | 9th |
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| 6/10/2023 | Macon Speedway - Macon, IL Ed Cain Trucking Hornet Challenge / Power Wheels Demo Derby DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Cliff Powell (Winged Outlaw) | 4th | - | - | 4th |
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| 6/16/2023 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association 305 Sprints - Winged, DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks | Results | | Cliff Powell (Winged Outlaw) | 3rd | - | - | 6th |
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| 6/23/2023 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets 410 Sprints - Winged, Winged Outlaw, Street Stocks | Results | | Cliff Powell (Winged Outlaw) | 4th | - | - | 9th |
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| 6/24/2023 | Macon Speedway - Macon, IL Illinois SPEED Week Midgets: POWRi National Midgets DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks | Results | | Cliff Powell (Winged Outlaw) | 5th | - | - | 11th |
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| 7/7/2023 | Macon Speedway - Macon, IL 410 Sprints - Non-Winged: USAC National Sprint Cars HART Non-Wing Micros | Results | | Cliff Powell (HART Non-Wing Micros) | 4th | - | - | 11th |
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| 7/15/2023 | Macon Speedway - Macon, IL POWRi Micros at Macon Speedway DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Cliff Powell (Winged Outlaw) | 6th | - | - | 8th |
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| 8/11/2023 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged, 305 Sprints - Winged, DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged Outlaw, Street Stocks | Results | | Cliff Powell (Winged Outlaw) | 7th | - | - | 11th |
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| 8/12/2023 | Macon Speedway - Macon, IL Throwback Sprint Cars / CEFCU Kids Club Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Non-Winged Sprints, Pro Late Model, Limited Modified, Dirt 6-cyl Stock Cars | Results | | Cliff Powell (Winged Outlaw) | 9th | - | - | 17th |
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| 9/1/2023 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged, 305 Sprints - Winged, Winged Outlaw, Street Stocks, 604 Crate Late Models | Results | | Cliff Powell (Winged Outlaw) | 6th | - | - | 14th |
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| 9/8/2023 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged, 305 Sprints - Winged, DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks | Results | | Cliff Powell (Winged Outlaw) | 5th | - | - | 9th |
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| 9/15/2023 | Jacksonville Speedway - Jacksonville, IL Xtreme Outlaw Midgets 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: Xtreme Outlaw Midgets Winged Outlaw, Street Stocks | Results | | Cliff Powell (Winged Outlaw) | 3rd | - | - | 11th |
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| 9/16/2023 | Macon Speedway - Macon, IL KERBYSTRONG Night featuring PLM, Modified, and Sportsman Specials / CEFCU Kids Club DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Hornets, Pro Late Model, HART Non-Wing Micros | Results | | Cliff Powell (HART Non-Wing Micros) | 7th | - | - | 7th |
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| 9/23/2023 | Macon Speedway - Macon, IL Brandt Season Championship "Racing for the Cup" DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Street Stocks, Hornets, Pro Late Model, Hybrid 600cc Micros | Results | | Cliff Powell (Hybrid 600cc Micros) | 8th | - | - | 12th |
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| 10/6/2023 | Jacksonville Speedway - Jacksonville, IL Ron Milton Race of Champions 410 Sprints - Winged: MOWA-Midwest Open Wheel Association 305 Sprints - Winged, DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks | Results | | Cliff Powell (Winged Outlaw) | 6th | - | - | 10th |
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| 10/21/2023 | Coles County Speedway - Mattoon, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Cliff Powell (Winged Outlaw) | DNS | - | DNS | - | | Cliff Powell (Winged A-Class) | 6th | - | DNS | - |
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