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| 1/24/2020 | Red Dirt Raceway - Meeker, OK Shawnee Indoor "Dash For Cash" with Outlaw Motorsports - Day 1 Junior Sprints, Junior Class, Junior 1 Medium Dirt Karts, Junior 1 Heavy Dirt Karts, Flat Adult Clone, Modified Animal, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Clone Heavy Dirt Karts, Clone Medium Dirt Karts, Clone Lite Dirt Karts, Clone Super Heavy Dirt Karts, Flat Jr. 1 Clone Heavy, Flat Jr. 2 Clone Heavy, Flat Jr. 1 Clone | Results | | Grayson Simmons (Modified Animal) | 6th (DNF) | - | - | - |
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| 1/25/2020 | Red Dirt Raceway - Meeker, OK Shawnee Indoor "Dash For Cash" with Outlaw Motorsports - Day 2 Junior Sprints, Junior Class, Junior 1 Medium Dirt Karts, Junior 1 Heavy Dirt Karts, Flat Adult Clone, Modified Animal, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Clone Heavy Dirt Karts, Clone Medium Dirt Karts, Clone Lite Dirt Karts, Clone Super Heavy Dirt Karts, Flat Jr. 1 Clone Heavy, Flat Jr. 2 Clone Heavy, Flat Jr. 1 Clone | Results | | Grayson Simmons (Modified Animal) | 1st | - | - | 2nd |
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| 2/7/2020 | Heart Of Oklahoma Speedway - Shawnee, OK 3rd Annual Doug Cottrell Memorial Young Guns, Junior Champ, Junior 1 Medium Dirt Karts, Junior 1 Heavy Dirt Karts, Adult Heavy, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Cage Jr. 3 Clone, Flat RWYB, Flat Stock Flatheads Med, Flat Adult Clone Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Cage Jr. Sprints | Results | | Grayson Simmons (Junior 1 Heavy Dirt Karts) | 3rd | - | - | 11th (DNF) |
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| 2/8/2020 | Heart Of Oklahoma Speedway - Shawnee, OK 3rd Annual Doug Cottrell Memorial Young Guns, Junior Champ, Junior 1 Medium Dirt Karts, Junior 1 Heavy Dirt Karts, Adult Heavy, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Cage Jr. 3 Clone, Flat RWYB, Flat Stock Flatheads Med, Flat Adult Clone Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Cage Jr. Sprints | Results | | Grayson Simmons (Junior 1 Heavy Dirt Karts) | 1st | - | - | 1st |
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| 5/22/2020 | Boss Speedway Dirt Track - Lawton, OK Jr Sprint Special & Team Bike Races Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Winged Outlaw, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Cage Jr. 3 Clone, Cage Jr. Sprints, Kid Karts Dirt, Senior Micros | Results | | Grayson Simmons (Winged Outlaw) | 1st | - | - | 1st |
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| 8/10/2020 | English Creek Speedway - Knoxville, IA Outlaw Dirt Kart Nationals Night 1 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Grayson Simmons (Adult Medium) | 5th | - | - | - |
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| 8/11/2020 | English Creek Speedway - Knoxville, IA Outlaw Dirt Kart Nationals Night 2 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Grayson Simmons (Adult Medium) | - | - | - | 10th (DNF) |
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| 10/3/2020 | Boss Speedway Dirt Track - Lawton, OK 2020 The Big Kahuna Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Winged Outlaw, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Cage Jr. 3 Clone, Kid Karts Dirt, Senior Micros | Results | | Grayson Simmons (Winged Outlaw) | 5th (DNF) | - | - | 3rd |
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| 11/6/2020 | Heart Of Oklahoma Speedway - Shawnee, OK Richard Kluver Memorial Race Young Guns, Junior Champ, Junior 1 Medium Dirt Karts, Junior 1 Heavy Dirt Karts, Adult Heavy, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Cage Jr. 3 Clone, Flat RWYB, Flat Stock Flatheads Med, Flat Adult Clone Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Cage Jr. Sprints | Results | | Grayson Simmons (Junior 1 Heavy Dirt Karts) | 1st | - | - | 1st | | Grayson Simmons (250 Winged Outlaw) | 6th | - | 10th | - |
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| 11/7/2020 | Heart Of Oklahoma Speedway - Shawnee, OK Richard Kluver Memorial Race Young Guns, Junior Champ, Junior 1 Medium Dirt Karts, Junior 1 Heavy Dirt Karts, Adult Heavy, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Cage Jr. 3 Clone, Flat RWYB, Flat Stock Flatheads Med, Flat Adult Clone Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Cage Jr. Sprints | Results | | Grayson Simmons (Junior 1 Heavy Dirt Karts) | 1st | - | - | 8th (DNF) | | Grayson Simmons (250 Winged Outlaw) | 3rd | - | - | 11th (DNF) |
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| 11/20/2020 | Boss Speedway Dirt Track - Lawton, OK Oklahoma/Texas Clash!! Junior Sprints, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Cage Jr. 3 Clone, 250 Winged Outlaw, Kid Karts Dirt | Results | | Grayson Simmons (250 Winged Outlaw) | 4th | - | - | 4th (DNF) |
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| 11/27/2020 | Heart Of Oklahoma Speedway - Shawnee, OK Turkey Shootout Young Guns, Junior Champ, Junior 1 Medium Dirt Karts, Junior 1 Heavy Dirt Karts, Adult Heavy, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Cage Jr. 3 Clone, Flat RWYB, Flat Stock Flatheads Med, Flat Adult Clone Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Cage Jr. Sprints | Results | | Grayson Simmons (Junior 1 Heavy Dirt Karts) | 4th | - | - | 5th | | Grayson Simmons (250 Winged Outlaw) | 5th (DNF) | - | 5th | - |
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| 11/28/2020 | Heart Of Oklahoma Speedway - Shawnee, OK Turkey Sjootout Young Guns, Junior Champ, Junior 1 Medium Dirt Karts, Junior 1 Heavy Dirt Karts, Adult Heavy, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Cage Jr. 3 Clone, Flat RWYB, Flat Stock Flatheads Med, Flat Adult Clone Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Cage Jr. Sprints | Results | | Grayson Simmons (Junior 1 Heavy Dirt Karts) | 1st | - | - | 1st | | Grayson Simmons (250 Winged Outlaw) | 6th | - | 9th | - |
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| 12/11/2020 | Heart Of Oklahoma Speedway - Shawnee, OK Dash in the Dirt Young Guns, Junior Champ, Junior 1 Medium Dirt Karts, Junior 1 Heavy Dirt Karts, Adult Heavy, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Cage Jr. 3 Clone, Flat RWYB, Flat Stock Flatheads Med, Flat Adult Clone Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Cage Jr. Sprints | Results | | Grayson Simmons (Junior 1 Heavy Dirt Karts) | 1st | - | - | 1st |
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| 12/12/2020 | Heart Of Oklahoma Speedway - Shawnee, OK Dash in the Dirt Young Guns, Junior Champ, Junior 1 Medium Dirt Karts, Junior 1 Heavy Dirt Karts, Adult Heavy, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Cage Jr. 3 Clone, Flat RWYB, Flat Stock Flatheads Med, Flat Adult Clone Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Cage Jr. Sprints | Results | | Grayson Simmons (Junior 1 Heavy Dirt Karts) | 1st | - | - | 1st | | Grayson Simmons (250 Winged Outlaw) | 2nd | - | - | 11th (DNF) |
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| 12/28/2020 | Tulsa Expo Raceway - Tulsa, OK AM: Early Move-In / PM: Regular Move-In Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Grayson Simmons (Restricted 'A' Class) | - | - | - | - | | Grayson Simmons (Junior Sprints) | - | - | - | - |
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| 12/30/2020 | Tulsa Expo Raceway - Tulsa, OK Racing Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, 600cc Modifieds | Results | | Grayson Simmons (Restricted 'A' Class) | 8th | - | - | - |
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| 12/31/2020 | Tulsa Expo Raceway - Tulsa, OK Racing Winged Outlaw, Non-Wing Outlaw, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Grayson Simmons (Junior Sprints) | 4th | - | - | - |
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