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| 5/30/2020 | Southern Illinois Raceway - Marion, IL Points Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Jordan Clary (Winged Outlaw) | 4th | - | - | 5th |
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| 6/5/2020 | Coles County Speedway - Mattoon, IL Weekly Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Jordan Clary (Winged Outlaw) | - | - | - | 1st |
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| 6/6/2020 | 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 | | Jordan Clary (Winged Outlaw) | 4th | - | - | 6th |
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| 6/20/2020 | Southern Illinois Raceway - Marion, IL Performance Electronics Prelude to the Hustle Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Jordan Clary (Winged Outlaw) | 7th | - | 7th | - |
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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 | | Jordan Clary (Winged A-Class) | 5th | - | - | 17th (DNF) |
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| 8/22/2020 | Macon Speedway - Macon, IL Camfield Memorial Midgets: POWRi DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks, Hornets | Results | | Jordan Clary (Winged Outlaw) | 7th | - | 6th | 13th |
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| 8/23/2020 | Jacksonville Speedway - Jacksonville, IL POWRi Midgets and Micros at Jacksonville Speedway Midgets: POWRi Winged Outlaw | Results | | Jordan Clary (Winged Outlaw) | 7th | - | 3rd | 13th |
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| 8/28/2020 | Tri City Speedway - Granite City, IL MOWA 410 Winged Sprints/POWRi WAR Non-Wing Sprints/305 Winged Sprints/Winged Micros 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Non-Winged Sprints: POWRi WAR Sprints 305 Sprints - Winged, Winged Outlaw | Results | | Jordan Clary (Winged Outlaw) | 1st | - | - | 13th |
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| 9/18/2020 | Tri City Speedway - Granite City, IL "Fan Appreciation/Big Kids Night" 1/2 Price $8 LM/Mod/BMod/St Stocks/4-Cyl/Winged Micros DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Winged Outlaw, B Modifieds, Street Stocks | Results | | Jordan Clary (Winged Outlaw) | 1st | - | - | 1st |
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| 9/25/2020 | Wayne County Speedway - Wayne City, IL Trump 45 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Jordan Clary (Non-Wing Outlaw) | 4th | - | - | 19th |
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| 9/26/2020 | Wayne County Speedway - Wayne City, IL Trump 45 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints | Results | | Jordan Clary (Non-Wing Outlaw) | 1st | 7th | - | 15th |
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| 10/9/2020 | Wayne County Speedway - Wayne City, IL Jason Leffler Memorial Midgets: USAC National Midgets Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints | Results | | Jordan Clary (Non-Wing Outlaw) | 1st | - | - | 3rd |
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