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| 5/11/2019 | Boone Speedway - Boone, IA Harris Auto Racing Saturday Night Series Night 5 305 Sprints - Winged, Hobby Stocks, A Modifieds, B Modifieds, Street Stocks, 600cc Modifieds | Results | | Jake Greenwood (305 Sprints - Winged) | DNS | - | - | DNS |
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| 6/8/2019 | Boone Speedway - Boone, IA Karl Chevrolet Dirt Trucks / Harris Auto Racing Saturday Night Series Night 9 305 Sprints - Winged, Hobby Stocks, Dirt Mini Trucks, A Modifieds, B Modifieds, Street Stocks, 600cc Modifieds | Results | | Jake Greenwood (305 Sprints - Winged) | 5th | - | - | 11th (DNF) |
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| 6/22/2019 | Boone Speedway - Boone, IA Harris Auto Racing Saturday Night Series Night 11 305 Sprints - Winged, Hobby Stocks, A Modifieds, B Modifieds, Street Stocks, 600cc Modifieds | Results | | Jake Greenwood (305 Sprints - Winged) | 5th | - | - | 8th (DNF) |
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| 6/29/2019 | Boone Speedway - Boone, IA Casey's General Stores / IMCATV Super Saturday / Harris Auto Racing Saturday Night Series Night 12 305 Sprints - Winged, Hobby Stocks, A Modifieds, B Modifieds, Street Stocks, 600cc Modifieds | Results | | Jake Greenwood (305 Sprints - Winged) | 3rd | - | - | 8th |
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| 7/6/2019 | Boone Speedway - Boone, IA Harris Auto Racing Saturday Night Series Night 13 305 Sprints - Winged, Hobby Stocks, A Modifieds, B Modifieds, Street Stocks, 600cc Modifieds | Results | | Jake Greenwood (305 Sprints - Winged) | 4th | - | - | 7th (DNF) |
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| 7/13/2019 | Boone Speedway - Boone, IA Harris Auto Racing Saturday Night Series Night 14 305 Sprints - Winged, Hobby Stocks, A Modifieds, B Modifieds, Street Stocks, Dwarf, 600cc Modifieds | Results | | Jake Greenwood (305 Sprints - Winged) | 2nd | - | - | 8th (DNF) |
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| 7/27/2019 | Boone Speedway - Boone, IA Hawkeye Challenge Make-Up- RaceSaver Sprint Car Championship Night / Saturday Night Series 305 Sprints - Winged, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Street Stocks, 600cc Modifieds | Results | | Jake Greenwood (305 Sprints - Winged) | - | - | - | 7th (DNF) |
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| 8/5/2019 | Southern Iowa Speedway - Oskaloosa, IA 410 Sprints - Winged: IRA Interstate Racing Association 305 Sprints - Winged | Results | | Jake Greenwood (305 Sprints - Winged) | 8th | - | - | 14th |
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| 9/20/2019 | Jackson Motorplex - Jackson, MN Casey's Open Wheel Nationals presented by Seafoam 410 Sprints - Winged: IRA Interstate Racing Association Non Wing Crate Sprints: Wisconsin wingLESS Sprints 305 Sprints - Winged, 360 Sprints - Non-Winged | Results | | Jake Greenwood (410 Sprints - Winged) | - | - | - | - | | Jake Greenwood (305 Sprints - Winged) | 7th | - | 8th | - |
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| 9/21/2019 | Jackson Motorplex - Jackson, MN Casey's Open Wheel Nationals presented by Seafoam 410 Sprints - Winged: IRA Interstate Racing Association Non Wing Crate Sprints: Wisconsin wingLESS Sprints 305 Sprints - Winged, 360 Sprints - Non-Winged | Results | | Jake Greenwood (305 Sprints - Winged) | 7th | - | 12th (DNF) | - |
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| 10/10/2019 | US 36 Raceway - Osborn, MO Missouri IMCA Nationals Night #1 305 Sprints - Winged, Stock Cars, A Modifieds, Limited Sport Mod | Postponed |
| 10/26/2019 | US 36 Raceway - Osborn, MO Missouri IMCA Nationals 305 Sprints - Winged, Stock Cars, A Modifieds, B Modifieds, Limited Sport Mod, Pure Stock | Results | | Jake Greenwood (305 Sprints - Winged) | 6th | - | - | 8th |
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