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| 5/10/2019 | Chateau Speedway - Lansing, MN Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Bobby Ruehlow (Winged Outlaw) | 4th | - | - | 4th |
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| 5/26/2019 | Chateau Speedway - Lansing, MN Spirit of 83 Memorial Winged Outlaw, Pure Stock, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Hornet | Results | | Bobby Ruehlow (Winged Outlaw) | 2nd | - | - | 6th |
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| 5/31/2019 | Chateau Speedway - Lansing, MN Kids Night-car rides and bike give away Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Bobby Ruehlow (Winged Outlaw) | 3rd | - | - | 8th |
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| 6/7/2019 | Chateau Speedway - Lansing, MN Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Bobby Ruehlow (Winged Outlaw) | 6th | - | - | 8th (DNF) |
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| 6/19/2019 | Stuart Speedway - Stuart, IA Weekly Racing Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Street Stocks, 600cc Modifieds, Limited Sport Mod, Sport Compact | Results | | Bobby Ruehlow (600cc Modifieds) | 3rd | - | - | 7th |
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| 6/20/2019 | Kossuth County Speedway - Algona, IA Micro Mods Hobby Stocks, A Modifieds, B Modifieds, Street Stocks, 600cc Modifieds, Enduro, Sport Compact | Results | | Bobby Ruehlow (600cc Modifieds) | 8th (DNF) | - | - | 7th |
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| 6/21/2019 | Chateau Speedway - Lansing, MN Inaugural Chateau Hall Of Fame Induction Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Bobby Ruehlow (Winged Outlaw) | 1st | - | - | 16th (DNF) |
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| 7/12/2019 | Chateau Speedway - Lansing, MN Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Bobby Ruehlow (Winged Outlaw) | 3rd | - | - | 9th (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 | | Bobby Ruehlow (Dwarf) | 2nd | - | - | 7th |
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| 7/19/2019 | Chateau Speedway - Lansing, MN Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Bobby Ruehlow (Winged Outlaw) | 6th | - | - | 4th |
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| 8/2/2019 | Chateau Speedway - Lansing, MN Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Bobby Ruehlow (Winged Outlaw) | 3rd | - | - | 1st |
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| 8/9/2019 | Chateau Speedway - Lansing, MN Pack The Stands $5 admission Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Bobby Ruehlow (Winged Outlaw) | 3rd | - | - | 9th |
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| 8/30/2019 | Chateau Speedway - Lansing, MN Season Championship Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Bobby Ruehlow (Winged Outlaw) | 2nd | - | - | 2nd |
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| 9/15/2019 | Mason City Motor Speedway - Mason City, IA New & Improved Season Opener 600cc Modifieds, USRA B-Mods, USRA Hobby Stocks, USRA Stock Cars | Results | | Bobby Ruehlow (600cc Modifieds) | 3rd | - | - | 3rd |
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| 9/27/2019 | Chateau Speedway - Lansing, MN Autumn Extravaganza Night 1 Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Bobby Ruehlow (Winged Outlaw) | 3rd | - | - | 6th |
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| 9/28/2019 | Chateau Speedway - Lansing, MN Autumn Extravaganza Night 2 Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Bobby Ruehlow (Winged Outlaw) | 3rd | - | - | 8th |
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