| | Heat | Dash | B Feature | A Feature |
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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 | | Aarin Squires (Restricted 'A' Class) | 6th (DNF) | - | - | DNS |
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| 6/13/2020 | Macon Speedway - Macon, IL Illinois SPEED Week Midgets: POWRi DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Aarin Squires (Winged A-Class) | 9th | - | - | DNS |
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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 | | Aarin Squires (Winged A-Class) | 7th | - | - | 14th (DNF) |
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| 8/8/2020 | Macon Speedway - Macon, IL Regular Night of Racing at Mighty Macon Speedway DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Aarin Squires (Winged A-Class) | 6th | - | - | 17th |
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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 | | Aarin Squires (Winged Outlaw) | 9th | - | - | 8th |
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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 | | Aarin Squires (Non-Wing Outlaw) | 7th | - | - | 7th |
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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 | | Aarin Squires (Winged A-Class) | 5th | - | - | 11th (DNF) |
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| 10/9/2020 | Jacksonville Speedway - Jacksonville, IL Ron Milton Race of Champions Midgets: POWRi 410 Sprints - Winged, Winged Outlaw | Results | | Aarin Squires (Winged Outlaw) | 8th | - | 17th | - |
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