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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 | | Charlie Olsen (Dirt Late Models) | 3rd | - | - | 5th |
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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 | | Charlie Olsen (Dirt Late Models) | 5th | - | - | 15th |
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| 5/28/2023 | Casino Speedway - Watertown, SD 8th Annual Casino Speedway Memorial Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Hornet | Results | | Charlie Olsen (Economy Late Models) | 4th | - | - | 4th |
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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 | | Charlie Olsen (Dirt Late Models) | 5th | - | 1st | 17th (DNF) |
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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 | | Charlie Olsen (Dirt Late Models) | 7th | - | 7th (DNF) | - |
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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 | | Charlie Olsen (Dirt Late Models) | 5th | - | - | 14th |
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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 | | Charlie Olsen (WISSOTA Late Model) | 4th | - | - | 17th (DNF) |
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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 | | Charlie Olsen (WISSOTA Late Model) | 6th | - | - | 16th |
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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 | | Charlie Olsen (USRA Late Models) | 1st | - | - | 19th (DNF) |
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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 | | Charlie Olsen (USRA Late Models) | 5th | - | - | 4th |
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| 6/17/2023 | Cedar Lake Speedway - New Richmond, WI 24th Annual Masters (Day 3 of 3) A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA Late Models | Results | | Charlie Olsen (USRA Late Models) | 5th | - | - | 6th |
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| 6/24/2023 | Madison Speedway - Madison, MN Race Night Stock Cars, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Rain Out |
| 7/7/2023 | Red Cedar Speedway - Menomonie, WI RCS VS MTS Showdown Open Modified & Open BMod Special w/USRA LM by Dean & Sues and Design Built St A Modifieds, B Modifieds, USRA Late Models, WISSOTA Super Stock | Results | | Charlie Olsen (USRA Late Models) | 2nd | - | - | 1st |
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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 | | Charlie Olsen (Dirt Late Models) | 5th (DNF) | - | 2nd | 12th |
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| 7/15/2023 | Cedar Lake Speedway - New Richmond, WI CLS Dash Race #9 / 5K to win Super Stocks Midwest Modifieds, 305 Sprints - Non-Winged, 600cc Modifieds, USRA Late Models, WISSOTA Super Stock | Results | | Charlie Olsen (USRA Late Models) | 1st | - | - | 1st |
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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 | | Charlie Olsen (Dirt Late Models) | 1st | - | - | - |
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| 7/20/2023 | Renegade Speedway - Canby, MN Yellow Medicine County Fair WISSOTA Street Stock: Street Stock Tour Pure Stock, WISSOTA Midwest Mods, WISSOTA Hornet, Dirt Limited Late Models | Results | | Charlie Olsen (Dirt Limited Late Models) | 6th | - | - | 9th (DNF) |
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| 7/30/2023 | Casino Speedway - Watertown, SD Macksteel | Skor Welding Kid's Night Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Hornet | Results | | Charlie Olsen (Economy Late Models) | 1st | - | - | 1st |
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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 | | Charlie Olsen (Dirt Late Models) | 8th (DNF) | - | 10th (DNF) | - |
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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 | | Charlie Olsen (Dirt Late Models) | 4th | - | - | 15th |
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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 | | Charlie Olsen (Dirt Late Models) | 10th (DNF) | - | 14th (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 | | Charlie Olsen (Dirt Late Models) | 2nd | - | - | 11th |
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| 9/3/2023 | Casino Speedway - Watertown, SD Busch Light Draw/Re-Draw Showdown Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Hornet | Results | | Charlie Olsen (Economy Late Models) | 3rd | - | - | 1st | | Charlie Olsen (WISSOTA Late Model) | 5th | - | - | 4th |
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| 9/30/2023 | Madison Speedway - Madison, MN Madtown Showdown Night 2 Stock Cars, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Rain Out |
| 10/1/2023 | Madison Speedway - Madison, MN Stock Cars, Economy Late Models, Open Dirt Karts, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet, Flat Jr. 2 Clone Heavy | Results | | Charlie Olsen (Economy Late Models) | 4th | - | - | 1st |
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| 10/7/2023 | Ogilvie Raceway - Ogilvie, MN Fall Classic presented by FYE Motorsports A Modifieds, USRA Late Models, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Charlie Olsen (USRA Late Models) | 1st | - | - | 2nd |
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