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| 4/16/2021 | Tri City Speedway - Granite City, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association DIRTcar Late Models, DIRTcar UMP Modifieds, Winged Outlaw | Results | | Aarin Squires (Winged Outlaw) | 7th | - | - | DNS |
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| 4/17/2021 | Highland Speedway - Highland, IL DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Aarin Squires (Winged Outlaw) | 6th | - | - | - |
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| 4/30/2021 | Tri City Speedway - Granite City, IL Fast Friday Racing UMP LM, UMP Mods, BMods, UMP St Stk, UMP 4-Cyl & Winged Micros DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Winged Outlaw, B Modifieds, Street Stocks | Results | | Aarin Squires (Winged Outlaw) | 5th | - | - | 11th |
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| 5/1/2021 | Macon Speedway - Macon, IL CEFCU Kid's Club Regular Night of Racing DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Aarin Squires (Winged A-Class) | 2nd | - | - | 20th (DNF) |
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| 8/28/2021 | Macon Speedway - Macon, IL Skeff Distributing presents IMRA Midgets / Hornet World Championships Economy Midgets, DIRTcar UMP Modifieds, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Aarin Squires (Winged A-Class) | 6th | - | - | 10th |
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| 9/10/2021 | Jacksonville Speedway - Jacksonville, IL Herb Barlow Memorial 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Aarin Squires (Winged Outlaw) | 7th | - | - | 15th |
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| 9/11/2021 | Macon Speedway - Macon, IL 98.1 Griz FM night featuring Vintage Racing of Ilinois Macon Speedway Hall of Fame Drivers DIRTcar UMP Modifieds, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Aarin Squires (Winged A-Class) | 7th | - | - | 13th (DNF) |
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| 10/9/2021 | US 24 Speedway - Logansport, IN Keyon Midgets + reg. program A-Wing $300 to win Midgets, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Senior Micros | Results | | Aarin Squires (Stock Non-Wing) | 10th | - | 13th (DNF) | - |
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| 10/23/2021 | US 24 Speedway - Logansport, IN Final race of the season. Awards to be handed out Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Senior Micros | Results | | Aarin Squires (Stock Non-Wing) | 7th | - | 5th | 15th |
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| 12/18/2021 | National Equestrian Center Raceway - St. Louis, MO Clash at the Coliseum Race #2 (Saturday) Kid Karts Dirt: Clash at the Coliseum Winged Outlaw, Rookie Class, Junior 2 Animal Dirt Karts, Restricted Box Stock, Unrestricted Box Stock, Junior Honda, Junior Animal, Senior Honda, Light 160, Flat RWYB, 500 Winged Open Outlaw, Clone Heavy Dirt Karts, Clone Medium Dirt Karts, Clone Super Heavy Dirt Karts, Blue Rookie, Red Rookie, Cage Jr. Predator, LO 206 Cage Junior 1 Winged, Flat Jr. 1 Clone, Predator Maxxis | Results | | Aarin Squires (Light 160) | 3rd | - | - | 4th |
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| 12/19/2021 | National Equestrian Center Raceway - St. Louis, MO Clash at the Coliseum Race #2 (Sunday) Kid Karts Dirt: Clash at the Coliseum Winged Outlaw, Rookie Class, Junior 2 Animal Dirt Karts, Restricted Box Stock, Unrestricted Box Stock, Junior Honda, Junior Animal, Senior Honda, Light 160, Flat RWYB, 500 Winged Open Outlaw, Clone Heavy Dirt Karts, Clone Medium Dirt Karts, Clone Super Heavy Dirt Karts, Blue Rookie, Red Rookie, Cage Jr. Predator, LO 206 Cage Junior 1 Winged, Flat Jr. 1 Clone, Predator Maxxis | Results | | Aarin Squires (Light 160) | 1st | - | - | 2nd |
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