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| 6/4/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #5 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Brayden Shepherd (Winged Outlaw) | 2nd | - | - | 14th |
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| 6/19/2021 | Newton Kart Klub - Newton, IA NKK Points Night #5 Winged Outlaw, Junior Class, Junior Champ, Junior 1 Lites Dirt Karts, Junior 1 Medium Dirt Karts, Junior 2 Lites Dirt Karts, Junior 2 Medium Dirt Karts, Junior 2 Heavy Dirt Karts, Junior Open, Rookie Class, Junior 1 Animal Dirt Karts, Junior 2 Animal Dirt Karts, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Open Speedway Midget, Restricted Box Stock, Unrestricted Box Stock, 125 Yamaha, Cage Stock Animal, 250 Winged Outlaw Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior 3 Heavy Dirt Karts, Quad A Class | Results | | Brayden Shepherd (500 Winged Open Outlaw) | 3rd | - | - | 3rd |
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| 7/2/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #8 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Brayden Shepherd (Winged Outlaw) | 1st | - | - | 3rd |
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| 7/16/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #9 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Brayden Shepherd (Winged Outlaw) | 2nd | - | - | 4th |
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| 7/23/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #10 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Brayden Shepherd (Winged Outlaw) | 1st | - | - | 14th (DNF) |
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| 7/30/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #11 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Rain Out |
| 8/9/2021 | English Creek Speedway - Knoxville, IA 2021 OUTLAW DIRT KART NATIONALS Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Brayden Shepherd (Winged Outlaw) | 1st | - | - | - |
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| 8/10/2021 | English Creek Speedway - Knoxville, IA 2021 OUTLAW DIRT KART NATIONALS Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Brayden Shepherd (Winged Outlaw) | - | 2nd | - | 2nd |
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| 8/22/2021 | Poplar Grove Speedway - Kamrar, IA Track Points Race Junior Class, Junior Champ, Winged Outlaw, Adult Open, Rookie Class, Dirt Cage Kart Junior 2, Cage Jr. 2 Clone, Flat Adult Clone, Unrestricted Box Stock, 125 Yamaha, Flat Adult Clone Heavy, Kid Karts Dirt, LO 206 Dirt Karts, Asphalt Sprint - LO206 Junior, LO 206 Cage Adult Winged, LO 206 Cage Cadet Winged, Flat Jr. 1 Clone Heavy, Flat Jr. 2 Clone Heavy | Results | | Brayden Shepherd (LO 206 Cage Adult Winged) | DNS | - | - | 3rd |
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