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| 5/31/2019 | Jackson Motorplex - Jackson, MN Ag Builders Night presented by GDF Enterprises 360 Sprints - Winged: Midwest Sprint Touring Series with Midwest Power Series 360 Sprints - Non-Winged: MBTS Non-Wing Sprints 305 Sprints - Winged | Results | | Bill Boles (360 Sprints - Winged) | 6th | - | 9th | - |
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| 6/7/2019 | Jackson Motorplex - Jackson, MN Military Night presented by American Auto Awards 360 Sprints - Winged: Midwest Sprint Touring Series with Midwest Power Series 360 Sprints - Non-Winged: MBTS Non-Wing Sprints 305 Sprints - Winged | Results | | Bill Boles (360 Sprints - Winged) | 7th | - | 4th | 15th |
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| 6/8/2019 | Fairmont Raceway - Fairmont, MN Danny Williams Memorial - Plus 360 Sprints and Kids Hunting Night 360 Sprints - Winged, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Sport Compact | Results | | Bill Boles (360 Sprints - Winged) | - | - | - | 1st |
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| 6/14/2019 | Rapid Speedway - Rock Rapids, IA Weekly Racing Series + MSTS 360 Sprints 360 Sprints - Winged: Midwest Sprint Touring Series DIRTcar Sportsmans, USRA B-Mods, USRA Hobby Stocks, USRA Stock Cars | Results | | Bill Boles (360 Sprints - Winged) | 1st | - | - | 5th |
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| 6/27/2019 | Jackson Motorplex - Jackson, MN 41st annual AGCO Jackson Nationals 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Bill Boles (305 Sprints - Winged) | 6th | - | - | 19th |
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| 6/28/2019 | Jackson Motorplex - Jackson, MN 41st annual AGCO Jackson Nationals 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Bill Boles (305 Sprints - Winged) | 6th | - | - | 19th |
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| 7/6/2019 | I-90 Speedway - Hartford, SD 360 Sprints - Winged: Midwest Sprint Touring Series 305 Sprints - Winged, Street Stocks, USRA B-Mods, USRA Hobby Stocks | Results | | Bill Boles (360 Sprints - Winged) | 6th | - | - | 11th |
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| 7/12/2019 | Jackson Motorplex - Jackson, MN New Fashion Pork Night 360 Sprints - Winged: Midwest Sprint Touring Series with Midwest Power Series 360 Sprints - Non-Winged: MBTS Non-Wing Sprints 305 Sprints - Winged | Results | | Bill Boles (360 Sprints - Winged) | 5th | - | 5th | - |
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| 7/19/2019 | Jackson Motorplex - Jackson, MN Livewire Printing Company Night- Barb Wieskus Memorial 360 Sprints - Winged: Midwest Sprint Touring Series with Midwest Power Series 305 Sprints - Winged, 360 Sprints - Non-Winged | Results | | Bill Boles (360 Sprints - Winged) | 1st | 5th | - | 20th |
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| 7/26/2019 | Jackson Motorplex - Jackson, MN Tony Stewart Night Presented by C&B Operations 410 Sprints - Winged: All Star Circuit of Champions 305 Sprints - Winged | Results | | Bill Boles (305 Sprints - Winged) | 6th | - | - | 10th |
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| 8/17/2019 | Jackson Motorplex - Jackson, MN Glenn Gillund Night 360 Sprints - Winged: Midwest Sprint Touring Series with Midwest Power Series 360 Sprints - Non-Winged: MBTS Non-Wing Sprints 305 Sprints - Winged | Results | | Bill Boles (360 Sprints - Winged) | 3rd | - | - | 15th |
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| 8/30/2019 | Jackson Motorplex - Jackson, MN 360 Nationals presented by Holiday Inn- Fairmont 360 Sprints - Winged: Midwest Sprint Touring Series with Midwest Power Series 360 Sprints - Non-Winged: MBTS Non-Wing Sprints | Results | | Bill Boles (360 Sprints - Winged) | 5th | - | 10th | - |
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| 8/31/2019 | Jackson Motorplex - Jackson, MN 360 Nationals- Paul Jerousek Memorial Presented by Spencer Radio Group 360 Sprints - Winged: Midwest Sprint Touring Series with Midwest Power Series 360 Sprints - Non-Winged: MBTS Non-Wing Sprints | Results | | Bill Boles (360 Sprints - Winged) | 6th | - | 11th | - |
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| 9/1/2019 | Jackson Motorplex - Jackson, MN 360 Nationals Presented by Sea Foam 360 Sprints - Winged: Midwest Sprint Touring Series with Midwest Power Series 360 Sprints - Non-Winged: MBTS Non-Wing Sprints | Results | | Bill Boles (360 Sprints - Winged) | 6th | - | 10th | - |
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