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| 4/30/2021 | US 36 Raceway - Osborn, MO Season Points Opener 305 Sprints - Winged, Stock Cars, A Modifieds, B Modifieds, Limited Sport Mod | Results | | Jake Greenwood (305 Sprints - Winged) | 7th | - | - | 6th |
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| 5/7/2021 | Crawford County Speedway - Denison, IA Regular Night All Classes-$1000 to win Modified 305 Sprints - Winged, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets, Sport Compact | Results | | Jake Greenwood (305 Sprints - Winged) | 5th | - | - | 7th |
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| 5/21/2021 | Crawford County Speedway - Denison, IA Regular Night All Classes-$1000 to win Sport Mods and Stocks Cars with draw/redraw for these classes 305 Sprints - Winged, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets, Sport Compact | Results | | Jake Greenwood (305 Sprints - Winged) | 2nd | - | - | 4th |
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| 5/28/2021 | Crawford County Speedway - Denison, IA Regular Night All Classes-$600 to win Hobby Stock and $400 to win Sport Compact 305 Sprints - Winged, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets, Sport Compact | Results | | Jake Greenwood (305 Sprints - Winged) | 7th | - | - | 15th (DNF) |
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| 6/4/2021 | Crawford County Speedway - Denison, IA Regular Night All Classes-$1000 to win Modifieds 305 Sprints - Winged, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets, Sport Compact | Results | | Jake Greenwood (305 Sprints - Winged) | 4th | - | - | 8th |
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| 6/11/2021 | Crawford County Speedway - Denison, IA Regular Night All Classes-$1000 to win Modified and Sprint Cars. Sponsored by Finishline 305 Sprints - Winged, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets, Sport Compact | Results | | Jake Greenwood (305 Sprints - Winged) | DNS | - | - | 12th (DNF) |
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| 6/18/2021 | Crawford County Speedway - Denison, IA Regular Night All Classes-$1000 to win Stock Cars 305 Sprints - Winged, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets, Sport Compact | Results | | Jake Greenwood (305 Sprints - Winged) | 3rd | - | - | 3rd |
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| 6/25/2021 | Crawford County Speedway - Denison, IA $1,500 to win at Crawford County Speedway 305 Sprints - Winged, Dirt Super Late Models, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets | Results | | Jake Greenwood (305 Sprints - Winged) | 1st | - | - | 1st |
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| 7/2/2021 | Crawford County Speedway - Denison, IA Regular Night All Classes-$600 to win Hobby Stock and $400 to win Sport Compact 305 Sprints - Winged, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets | Results | | Jake Greenwood (305 Sprints - Winged) | 4th | - | - | 3rd |
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| 7/9/2021 | Crawford County Speedway - Denison, IA Regular Night All Classes-$1000 to win Stock Cars 305 Sprints - Winged, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets | Results | | Jake Greenwood (305 Sprints - Winged) | 3rd | - | - | 4th |
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| 7/16/2021 | Crawford County Speedway - Denison, IA Regular Night All Classes-$1000 to win Sport Mods 305 Sprints - Winged, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets | Results | | Jake Greenwood (305 Sprints - Winged) | 2nd | - | - | 4th |
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| 7/21/2021 | Buena Vista Raceway - Alta, IA Sprint Car Special 305 Sprints - Winged, Hobby Stocks, Stock Cars, B Modifieds, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Jake Greenwood (305 Sprints - Winged) | 2nd | - | - | 6th |
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| 7/23/2021 | Crawford County Speedway - Denison, IA Regular Night All Classes-Fair Night 305 Sprints - Winged, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets | Results | | Jake Greenwood (305 Sprints - Winged) | 3rd | - | - | 5th |
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| 7/24/2021 | Bethany Fairgrounds Speedway - Bethany, MO URSS Wing Sprints A Modifieds, B Modifieds, Street Stocks, 360 Sprints - Non-Winged, Pure Stock | Rain Out |
| 7/30/2021 | Crawford County Speedway - Denison, IA Regular Night All Classes-$1000 to win Modified 305 Sprints - Winged, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets | Rain Out |
| 8/6/2021 | Crawford County Speedway - Denison, IA Regular Night All Classes-$1000 to win Sprint Cars 305 Sprints - Winged, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets | Results | | Jake Greenwood (305 Sprints - Winged) | 4th | - | - | 12th |
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| 8/13/2021 | Crawford County Speedway - Denison, IA Regular Night All Classes-$600 to win Hobby Stock and $400 to win Sport Compact 305 Sprints - Winged, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets | Results | | Jake Greenwood (305 Sprints - Winged) | 2nd | - | - | 8th (DNF) |
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| 8/27/2021 | US 36 Raceway - Osborn, MO Regular Season Racing 305 Sprints - Winged, Stock Cars, A Modifieds, B Modifieds, Limited Sport Mod, Pure Stock | Results | | Jake Greenwood (305 Sprints - Winged) | 2nd | - | - | 11th (DNF) |
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| 10/7/2021 | US 36 Raceway - Osborn, MO IMCA Missouri Nationals Test 'n' Tune Night 305 Sprints - Winged, Stock Cars, A Modifieds, B Modifieds, Limited Sport Mod, Pure Stock | Results | | Jake Greenwood (305 Sprints - Winged) | - | - | - | - |
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| 10/8/2021 | US 36 Raceway - Osborn, MO IMCA Missouri Nationals 305 Sprints - Winged, Stock Cars, A Modifieds, B Modifieds, Limited Sport Mod, Pure Stock | Results | | Jake Greenwood (305 Sprints - Winged) | 6th | - | 6th | - |
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| 10/9/2021 | US 36 Raceway - Osborn, MO IMCA Missouri Nationals 305 Sprints - Winged, Stock Cars, A Modifieds, B Modifieds, Limited Sport Mod, Pure Stock | Results | | Jake Greenwood (305 Sprints - Winged) | - | - | - | 13th |
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