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| 5/4/2019 | Cedar Lake Speedway - New Richmond, WI 360 Sprints - Winged: Midwest Power Series A Modifieds, Midwest Modifieds, Dirt Late Models, Super Stocks, USRA Late Models | Results | | Ryan Bowers (360 Sprints - Winged) | 3rd | 4th | - | 3rd |
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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 | | Ryan Bowers (360 Sprints - Winged) | 3rd | - | 2nd | 16th |
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| 6/1/2019 | Knoxville Raceway - Knoxville, IA 360 Sprints - Winged: Nebraska 360 sprints with Midwest Power Series 410 Sprints - Winged, 305 Sprints - Winged | Results | | Ryan Bowers (360 Sprints - Winged) | 1st | - | - | 20th |
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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 | | Ryan Bowers (360 Sprints - Winged) | 7th (DNF) | - | DNS | - |
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| 6/22/2019 | Ogilvie Raceway - Ogilvie, MN Midwest Power Series Sprint Car Special 360 Sprints - Winged: Midwest Power Series 360 Sprints - Non-Winged: MBTS Non-Wing Sprints WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Hornet | Results | | Ryan Bowers (360 Sprints - Winged) | 5th | - | - | 11th |
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| 7/26/2019 | Princeton Speedway - Princeton, MN 360 Sprints - Non-Winged: MBTS Non-Wing Sprints Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Ryan Bowers (360 Sprints - Non-Winged) | 2nd | - | - | 1st |
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| 9/7/2019 | Cedar Lake Speedway - New Richmond, WI Richert Memorial 360 Sprints - Winged: Midwest Power Series 410 Sprints - Winged: IRA Interstate Racing Association 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series 305 Sprints - Non-Winged | Results | | Ryan Bowers (360 Sprints - Non-Winged) | 2nd | - | - | 2nd | | Ryan Bowers (305 Sprints - Non-Winged) | 2nd | - | - | 2nd |
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| 9/13/2019 | Cedar Lake Speedway - New Richmond, WI Legendary 100 night 2 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks | Results | | Ryan Bowers (360 Sprints - Non-Winged) | 8th | - | - | 24th | | Ryan Bowers (305 Sprints - Non-Winged) | 2nd | - | - | 24th |
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| 9/14/2019 | Cedar Lake Speedway - New Richmond, WI Legendary 100 night 3 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks | Results | | Ryan Bowers (360 Sprints - Non-Winged) | 1st | - | - | 1st | | Ryan Bowers (305 Sprints - Non-Winged) | 1st | - | - | 1st |
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| 9/19/2019 | Red Cedar Speedway - Menomonie, WI 40th Annual Punky Manor Night #1 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Dirt Super Late Models, Hornets, WISSOTA Pure Stock, WISSOTA Street Stock | Results | | Ryan Bowers (360 Sprints - Non-Winged) | 2nd | - | - | 4th |
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