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| 1/5/2019 | Arizona Speedway - Queen Creek, AZ Wild West Shootout Round 1 Dirt Super Late Models, A Modifieds, B Modifieds | Results | | Chad Olsen (A Modifieds) | 1st | - | - | 10th |
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| 1/6/2019 | Arizona Speedway - Queen Creek, AZ Wild West Shootout Round 2 Dirt Super Late Models, A Modifieds, B Modifieds | Results | | Chad Olsen (A Modifieds) | - | - | - | - |
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| 1/11/2019 | Arizona Speedway - Queen Creek, AZ Wild West Shootout Round 4 Dirt Super Late Models, A Modifieds, B Modifieds | Results | | Chad Olsen (A Modifieds) | 2nd | - | - | 17th |
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| 1/12/2019 | Arizona Speedway - Queen Creek, AZ Wild West Shootout Round 5 Dirt Super Late Models, A Modifieds, B Modifieds | Results | | Chad Olsen (A Modifieds) | 11th | - | 5th | - |
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| 1/13/2019 | Arizona Speedway - Queen Creek, AZ Wild West Shootout Round 6 Dirt Super Late Models, A Modifieds, B Modifieds | Results | | Chad Olsen (A Modifieds) | 7th | - | 7th | - |
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| 5/26/2019 | Casino Speedway - Watertown, SD WISSOTA Dirt Track Series Casino Speedway Memorial WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Chad Olsen (WISSOTA Late Model) | 4th | - | - | 5th |
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| 5/31/2019 | Brown County Speedway - Aberdeen, SD WISSOTA Late Model Challenge Series Race WISSOTA Late Model: Wissota Late Model Challenge Series Pure Stock, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Chad Olsen (WISSOTA Late Model) | 2nd | - | - | 11th |
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| 6/1/2019 | Madison Speedway - Madison, MN Stock Cars, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Chad Olsen (WISSOTA Modifieds) | 1st | - | - | 5th |
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| 6/9/2019 | Casino Speedway - Watertown, SD WISSOTA Dirt Track Series Weekly Race WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Chad Olsen (WISSOTA Modifieds) | 2nd | - | - | 3rd | | Chad Olsen (WISSOTA Late Model) | 4th | - | - | 9th |
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| 6/13/2019 | Clay County Fair Speedway - Spencer, IA Norgaard Sand & Gravel Tri-State Late Models Dirt Late Models: Tri-State Late Models Hobby Stocks, B Modifieds, Sport Compact | Results | | Chad Olsen (Dirt Late Models) | 1st | - | - | 7th |
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| 6/14/2019 | Jackson Motorplex - Jackson, MN Tri-State Late Models Dirt Late Models: Tri-State Late Models DIRTcar Late Models, Hobby Stocks, B Modifieds | Results | | Chad Olsen (DIRTcar Late Models) | - | - | - | - | | Chad Olsen (Dirt Late Models) | 1st | - | - | 3rd |
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| 6/16/2019 | Casino Speedway - Watertown, SD WISSOTA Dirt Track Series Father's Day Races WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Chad Olsen (WISSOTA Modifieds) | 1st | - | - | 11th | | Chad Olsen (WISSOTA Late Model) | 3rd | - | - | 5th |
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| 6/22/2019 | Madison Speedway - Madison, MN Stock Cars, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Rain Out |
| 7/3/2019 | Brown County Speedway - Aberdeen, SD 410 Sprints - Winged: World of Outlaws Dirt Late Models: Tri-State Late Models Pure Stock | Results | | Chad Olsen (Dirt Super Late Models) | - | - | - | - | | Chad Olsen (Dirt Late Models) | 1st | - | - | 24th |
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| 7/6/2019 | Madison Speedway - Madison, MN Stock Cars, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Chad Olsen (WISSOTA Modifieds) | 1st | - | - | 1st |
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| 7/13/2019 | Madison Speedway - Madison, MN Stock Cars, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Chad Olsen (WISSOTA Modifieds) | 4th | - | - | 1st |
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| 7/14/2019 | Casino Speedway - Watertown, SD WISSOTA Dirt Track Series Regular Race WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Chad Olsen (WISSOTA Modifieds) | 4th | - | - | 4th | | Chad Olsen (WISSOTA Late Model) | 1st | - | - | 4th |
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| 7/21/2019 | Casino Speedway - Watertown, SD AFCO Race of Champions Qualifier Race Night WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Chad Olsen (WISSOTA Modifieds) | 3rd | - | - | 8th | | Chad Olsen (WISSOTA Late Model) | 1st | - | - | 2nd |
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| 8/2/2019 | Fiesta City Speedway - Montevideo, MN Chippewa County Fair Races Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Chad Olsen (WISSOTA Modifieds) | 1st | - | - | 4th | | Chad Olsen (WISSOTA Late Model) | 4th | - | - | 2nd |
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| 8/4/2019 | Casino Speedway - Watertown, SD Advantage RV's Mod Tour Series Finale WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Chad Olsen (WISSOTA Modifieds) | 2nd | - | - | 11th | | Chad Olsen (WISSOTA Late Model) | 1st | - | - | 6th |
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| 8/10/2019 | Fiesta City Speedway - Montevideo, MN Late Model Special Night #2 Dirt Late Models: Tri-State Late Models Dirt Super Late Models, Factory Stocks, Economy Late Models, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Chad Olsen (Dirt Late Models) | 2nd | - | - | 1st |
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| 8/16/2019 | Fairmont Raceway - Fairmont, MN Fair Race with the Tri-State Late Models (Friday Night) Dirt Late Models: Tri-State Late Models Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Sport Compact | Results | | Chad Olsen (Dirt Late Models) | 1st | - | - | 1st |
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| 8/25/2019 | Casino Speedway - Watertown, SD 10th Annual USMTS Summer Slam/Sandy Benson Memorial A Modifieds: USMTS - United States Modified Touring Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock | Results | | Chad Olsen (A Modifieds) | 1st | - | - | 16th |
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| 9/20/2019 | Casino Speedway - Watertown, SD Autumn Classic Night #1 Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Chad Olsen (WISSOTA Modifieds) | 1st | - | - | 10th (DNF) | | Chad Olsen (WISSOTA Late Model) | 3rd | - | - | 20th |
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| 9/21/2019 | Casino Speedway - Watertown, SD Autumn Classic Night #2 Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Chad Olsen (WISSOTA Modifieds) | 1st | - | - | 1st | | Chad Olsen (WISSOTA Late Model) | 5th | - | - | 16th (DNF) |
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| 9/27/2019 | Madison Speedway - Madison, MN Madtown Showdown Night #1 Stock Cars, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Chad Olsen (WISSOTA Modifieds) | 1st | - | - | 8th |
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