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| 4/20/2019 | Beaver Dam Raceway - Beaver Dam, WI Wipperfurth Memorial 410 Sprints - Winged: IRA Interstate Racing Association Non Wing Crate Sprints: Wisconsin wingLESS Sprints Badger Midgets: Badger Midget Auto Racing Association | Results | | Greg Olsen (Non Wing Crate Sprints) | 3rd | - | - | 7th |
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| 5/4/2019 | Wilmot Raceway - Wilmot, WI 410 Sprints - Winged: IRA Interstate Racing Association Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Greg Olsen (Non Wing Crate Sprints) | 1st | - | - | 10th |
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| 5/25/2019 | Wilmot Raceway - Wilmot, WI Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Greg Olsen (Non Wing Crate Sprints) | 5th | - | - | 8th |
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| 5/26/2019 | 141 Speedway - Maribel, WI 410 Sprints - Winged: IRA Interstate Racing Association Lightning Sprints: Wisconsin Illinois Mini Sprints Non Wing Crate Sprints: Wisconsin wingLESS Sprints 360 Sprints - Winged, Non-Winged Sprints, Pro Legends, 1200cc Outlaws Winged Minis | Results | | Greg Olsen (Non Wing Crate Sprints) | 4th | - | - | 13th |
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| 6/8/2019 | Wilmot Raceway - Wilmot, WI Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Greg Olsen (Non Wing Crate Sprints) | 4th | - | - | 14th |
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| 6/15/2019 | Wilmot Raceway - Wilmot, WI Raymond Neeve Memorial 410 Sprints - Winged: IRA Interstate Racing Association Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Greg Olsen (Non Wing Crate Sprints) | 4th | - | - | 9th |
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| 6/22/2019 | Wilmot Raceway - Wilmot, WI Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Greg Olsen (Non Wing Crate Sprints) | 5th | - | - | 19th |
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| 6/23/2019 | Angell Park Speedway - Sun Prairie, WI Open Wheel Showdown Non Wing Crate Sprints: Wisconsin wingLESS Sprints Badger Midgets: Badger Midget Auto Racing Association Midgets, Masters Legends | Rain Out |
| 6/29/2019 | Wilmot Raceway - Wilmot, WI Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Greg Olsen (Non Wing Crate Sprints) | 4th | - | - | 7th |
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| 6/30/2019 | 141 Speedway - Maribel, WI 410 Sprints - Winged: IRA Interstate Racing Association Lightning Sprints: Wisconsin Illinois Mini Sprints Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Greg Olsen (Non Wing Crate Sprints) | 1st | - | - | 10th |
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| 7/6/2019 | Wilmot Raceway - Wilmot, WI Salute To Harry Turner Non Wing Crate Sprints: Wisconsin wingLESS Sprints Badger Midgets: Badger Midget Auto Racing Association | Results | | Greg Olsen (Non Wing Crate Sprints) | 1st | - | - | 10th |
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| 7/7/2019 | Angell Park Speedway - Sun Prairie, WI Pepsi Nationals Midgets: POWRi National Midgets Non Wing Crate Sprints: Wisconsin wingLESS Sprints Badger Midgets: Badger Midget Auto Racing Association Semi-Pro Legends, Masters Legends | Results | | Greg Olsen (Non Wing Crate Sprints) | 5th | - | - | 13th |
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| 7/27/2019 | Wilmot Raceway - Wilmot, WI Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Greg Olsen (Non Wing Crate Sprints) | 1st | - | - | 1st |
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| 8/17/2019 | Wilmot Raceway - Wilmot, WI Roger Iles Tribute at the Kenosha County Fair 410 Sprints - Winged: IRA Interstate Racing Association Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Greg Olsen (Non Wing Crate Sprints) | 4th | - | - | 11th |
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| 8/24/2019 | Wilmot Raceway - Wilmot, WI Non Wing Crate Sprints: Wisconsin wingLESS Sprints A Modifieds, Street Stocks, Hornets, Lightning Sprints | Results | | Greg Olsen (Non Wing Crate Sprints) | 1st | - | - | 3rd |
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| 8/30/2019 | Wilmot Raceway - Wilmot, WI 410 Sprints - Winged: IRA Interstate Racing Association Non Wing Crate Sprints: Wisconsin wingLESS Sprints Lightning Sprints | Results | | Greg Olsen (Non Wing Crate Sprints) | 1st | - | - | 5th |
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| 8/31/2019 | Wilmot Raceway - Wilmot, WI Non Wing Crate Sprints: Wisconsin wingLESS Sprints A Modifieds, Street Stocks, Lightning Sprints | Results | | Greg Olsen (Non Wing Crate Sprints) | 1st | - | - | - |
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| 9/1/2019 | Angell Park Speedway - Sun Prairie, WI Kevin Doty Classic Non Wing Crate Sprints: Wisconsin wingLESS Sprints Badger Midgets: Badger Midget Auto Racing Association Midgets | Results | | Greg Olsen (Non Wing Crate Sprints) | 1st | - | - | 22nd |
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| 9/7/2019 | Wilmot Raceway - Wilmot, WI Non Wing Crate Sprints: Wisconsin wingLESS Sprints A Modifieds, Street Stocks, Dirt Late Models | Results | | Greg Olsen (Non Wing Crate Sprints) | 3rd | - | - | 2nd |
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| 9/14/2019 | Beaver Dam Raceway - Beaver Dam, WI Scott Semmelmann Memorial 410 Sprints - Winged: IRA Interstate Racing Association Non Wing Crate Sprints: Wisconsin wingLESS Sprints Badger Midgets: Badger Midget Auto Racing Association | Results | | Greg Olsen (Non Wing Crate Sprints) | 3rd | - | - | 4th |
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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 | | Greg Olsen (360 Sprints - Non-Winged) | 3rd | - | - | 6th | | Greg Olsen (Non Wing Crate Sprints) | 3rd | - | - | 6th |
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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 | | Greg Olsen (360 Sprints - Non-Winged) | 4th | - | - | 6th | | Greg Olsen (Non Wing Crate Sprints) | 4th | - | - | 6th |
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| 9/28/2019 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI WI State Sprint Championships 360 Sprints - Winged: Midwest Sprint Car Association 410 Sprints - Winged: IRA Interstate Racing Association Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Greg Olsen (Non Wing Crate Sprints) | - | - | - | 17th |
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