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| 1/1/2021 | Tulsa Expo Raceway - Tulsa, OK Racing Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Grayson Simmons (Junior Sprints) | - | 2nd | - | - |
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| 1/2/2021 | Tulsa Expo Raceway - Tulsa, OK Driller Time! 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) | - | - | 1st | 7th |
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| 1/8/2021 | Heart Of Oklahoma Speedway - Shawnee, OK 4th Annual Outlaw Kart Superbowl 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 | - | - | - |
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| 1/9/2021 | Heart Of Oklahoma Speedway - Shawnee, OK 4th Annual Outlaw Kart Superbowl 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) | 2nd | - | - | 1st |
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| 2/5/2021 | Heart Of Oklahoma Speedway - Shawnee, OK 4th Annual Doug Cottrell 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) | 2nd | - | - | 9th (DNF) |
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| 2/6/2021 | Heart Of Oklahoma Speedway - Shawnee, OK 4th Annual Doug Cottrell 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 | - | 7th | - |
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| 3/26/2021 | Heart Of Oklahoma Speedway - Shawnee, OK Charlie Brown Showdown 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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| 3/27/2021 | Heart Of Oklahoma Speedway - Shawnee, OK Charlie Brown Showdown 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) | 2nd | - | - | 3rd | | Grayson Simmons (250 Winged Outlaw) | 3rd | - | - | 4th |
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| 5/22/2021 | I-44 Speedway Park - Oklahoma City, OK Weekly Points Race Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Grayson Simmons (Restricted 'A' Class) | 7th | - | - | 13th |
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| 6/19/2021 | I-44 Speedway Park - Oklahoma City, OK Weekly Points Race Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Rain Out |
| 7/17/2021 | I-44 Speedway Park - Oklahoma City, OK Weekly Points Race Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Stock Non-Wing, Junior Sprints | Canceled |
| 7/31/2021 | I-44 Speedway Park - Oklahoma City, OK Weekly Points Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Grayson Simmons (Restricted 'A' Class) | 3rd | - | - | 6th |
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| 8/14/2021 | I-44 Speedway Park - Oklahoma City, OK Weekly Points Race Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Grayson Simmons (Restricted 'A' Class) | 2nd | - | - | 17th (DNF) |
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| 10/2/2021 | Port City Raceway - Tulsa, OK RUJO Rumble - Final Points Night Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Hybrid 600cc Micros | Results | | Grayson Simmons (Restricted 'A' Class) | 7th | - | DNS | - |
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| 11/5/2021 | Heart Of Oklahoma Speedway - Shawnee, OK 2nd Annual Richard Kluver 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, 125 Winged Outlaw | Results | | Grayson Simmons (Junior 1 Heavy Dirt Karts) | 1st | - | - | 1st |
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| 11/6/2021 | Heart Of Oklahoma Speedway - Shawnee, OK 2nd Annual Richard Kluver 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, 125 Winged Outlaw | Results | | Grayson Simmons (250 Winged Outlaw) | 5th | - | DNS | - |
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| 11/26/2021 | 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, 125 Winged Outlaw | Results | | Grayson Simmons (Junior 1 Heavy Dirt Karts) | 2nd | - | - | 4th | | Grayson Simmons (250 Winged Outlaw) | 1st | - | - | 12th (DNF) |
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| 11/27/2021 | 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, 125 Winged Outlaw | Results | | Grayson Simmons (Junior 1 Heavy Dirt Karts) | 2nd | - | - | 1st | | Grayson Simmons (250 Winged Outlaw) | 5th (DNF) | - | DNS | - |
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| 12/10/2021 | 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, 125 Winged Outlaw | Results | | Grayson Simmons (Junior 1 Heavy Dirt Karts) | 2nd | - | - | 8th (DNF) |
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| 12/11/2021 | 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, 125 Winged Outlaw | Results | | Grayson Simmons (Junior 1 Heavy Dirt Karts) | 1st | - | - | 1st | | Grayson Simmons (250 Winged Outlaw) | 2nd | - | - | 8th (DNF) |
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