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| 5/25/2019 | Viking Speedway - Alexandria, MN Memorial Weekend Special Dirt Super Late Models, Dirt Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Richard Chasteen (WISSOTA Street Stock) | 9th | - | - | 23rd (DNF) |
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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 | | Richard Chasteen (WISSOTA Street Stock) | 8th | - | - | 8th (DNF) |
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| 6/29/2019 | Cedar Lake Speedway - New Richmond, WI CLS Dash Limited Sprints - Winged: UMSS Winged Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Richard Chasteen (USRA Late Models) | 6th (DNF) | - | - | 7th |
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| 7/13/2019 | Cedar Lake Speedway - New Richmond, WI Dash Race #8: Late Models, Modifieds, Pro Stocks, Limited Late Models and Midwest Mods A Modifieds, Midwest Modifieds, Dirt Late Models, Super Stocks, USRA Late Models | Results | | Richard Chasteen (USRA Late Models) | 6th | - | - | 7th |
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| 7/27/2019 | Cedar Lake Speedway - New Richmond, WI CLS Dash with Northern Renegades Limited Sprints - Winged: UMSS Winged Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Richard Chasteen (USRA Late Models) | 7th | - | - | 8th |
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| 8/1/2019 | Cedar Lake Speedway - New Richmond, WI Dirt Super Late Models: World of Outlaws - Late Models USRA Late Models | Results | | Richard Chasteen (USRA Late Models) | 9th | - | - | 15th |
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| 8/16/2019 | Red Cedar Speedway - Menomonie, WI 3rd Annual Mahder 55 Wissota Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series Dirt Super Late Models, WISSOTA Modifieds, WISSOTA Super Stock | Results | | Richard Chasteen (Dirt Super Late Models) | 6th | - | - | 15th |
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| 8/17/2019 | Cedar Lake Speedway - New Richmond, WI CLS Dash 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Richard Chasteen (USRA Late Models) | 5th | - | - | 5th |
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| 8/30/2019 | I-94 Speedway - Fergus Falls, MN Season Championship- LEIGHTON BROADCASTING and Valley Fab and Repair Hornets, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock | Results | | Richard Chasteen (WISSOTA Street Stock) | 7th (DNF) | - | - | 15th (DNF) |
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| 9/25/2019 | Hamilton County Speedway - Webster City, IA USRA Nationals Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets, USRA Modifieds, USRA Late Models | Rain Out |
| 10/4/2019 | Ogilvie Raceway - Ogilvie, MN MTH Fall Classic (FYE) Sport Compact, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Richard Chasteen (WISSOTA Street Stock) | 7th | - | 11th | - |
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