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| 5/19/2023 | Rapid Speedway - Rock Rapids, IA FILL THE FOODBANK + Tri-State Late Models Dirt Late Models: Tri-State Late Models Dirt Super Late Models, DIRTcar Sportsmans, USRA B-Mods, USRA Hobby Stocks, USRA Stock Cars | Results | | Chad Olsen (Dirt Late Models) | 1st | - | - | 2nd |
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| 5/20/2023 | I-90 Speedway - Hartford, SD Tri-State Late Models + RPM Race Series Dirt Late Models: Tri-State Late Models 305 Sprints - Winged, Dirt Super Late Models, B Modifieds, Street Stocks, USRA B-Mods, USRA Hobby Stocks, WISSOTA Late Model | Results | | Chad Olsen (Dirt Late Models) | 1st | - | - | 1st |
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| 5/29/2023 | Huset's Speedway - Brandon, SD Myrl & Roy's Paving Night Ben Nothdurft Memorial- presented by Bargain Barn Tire Center 410 Sprints - Winged: Northern Outlaw Sprint Association Dirt Late Models: Tri-State Late Models 360 Sprints - Winged, Dirt Super Late Models, IMCA RaceSaver Sprint Car, WISSOTA Late Model | Results | | Chad Olsen (Dirt Late Models) | 2nd | - | - | 4th |
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| 6/1/2023 | Dakota State Fair Speedway - Huron, SD Wheel Jam 2023 Dirt Late Models: Tri-State Late Models Dirt Super Late Models, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Street Stock | Results | | Chad Olsen (Dirt Late Models) | 2nd | - | - | 5th |
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| 6/3/2023 | Dakota State Fair Speedway - Huron, SD Wheel Jam 2023 Dirt Late Models: Tri-State Late Models Dirt Super Late Models, WISSOTA Midwest Mods, WISSOTA Late Model | Results | | Chad Olsen (Dirt Late Models) | 2nd | - | - | 17th |
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| 6/9/2023 | Fiesta City Speedway - Montevideo, MN Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series Factory Stocks, Dirt Late Models, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Hornet | Results | | Chad Olsen (WISSOTA Late Model) | 1st | - | - | 5th |
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| 6/10/2023 | Madison Speedway - Madison, MN Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series Stock Cars, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Hornet | Results | | Chad Olsen (WISSOTA Late Model) | 6th | - | - | 15th |
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| 6/15/2023 | Cedar Lake Speedway - New Richmond, WI 24th Annual Masters (Day 1 of 3) A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA Late Models | Results | | Chad Olsen (Dirt Late Models) | 4th | - | 2nd | 21st |
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| 6/16/2023 | Cedar Lake Speedway - New Richmond, WI 24th Annual Masters (Day 2 of 3) A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA Late Models | Results | | Chad Olsen (Dirt Late Models) | 8th | - | 9th | - |
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| 7/8/2023 | Park Jefferson International Speedway - Jefferson, SD Weekly Racing Dirt Late Models: Tri-State Late Models Dirt Super Late Models, B Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Chad Olsen (Dirt Late Models) | 1st | - | - | 3rd |
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| 7/19/2023 | Huset's Speedway - Brandon, SD Silver Dollar Nationals presented by MyRacePass Dirt Late Models: Tri-State Late Models IMCA Stock Car | Results | | Chad Olsen (Dirt Late Models) | 2nd | - | - | - |
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| 8/3/2023 | Cedar Lake Speedway - New Richmond, WI World of Outlaws USA Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Chad Olsen (Dirt Late Models) | 2nd | - | - | 9th |
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| 8/4/2023 | Cedar Lake Speedway - New Richmond, WI World of Outlaws USA Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Chad Olsen (Dirt Late Models) | 3rd | - | - | 24th (DNF) |
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| 8/5/2023 | Cedar Lake Speedway - New Richmond, WI World of Outlaws USA Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Chad Olsen (Dirt Late Models) | 1st | - | - | 20th (DNF) |
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| 8/19/2023 | Dakota State Fair Speedway - Huron, SD Dirt Late Models Dirt Late Models: Tri-State Late Models Dirt Super Late Models, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Chad Olsen (Dirt Late Models) | 6th (DNF) | - | - | 9th |
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