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| 5/5/2023 | Fiesta City Speedway - Montevideo, MN Season Opener Factory Stocks, B Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jon Tollakson (WISSOTA Late Model) | 1st | - | - | 7th |
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| 5/12/2023 | Fiesta City Speedway - Montevideo, MN Regular Race Night Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jon Tollakson (WISSOTA Late Model) | 4th | - | - | 4th |
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| 5/19/2023 | I-94 Speedway - Fergus Falls, MN Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series Hornets, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Jon Tollakson (WISSOTA Late Model) | 5th | - | 3rd | 20th |
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| 5/20/2023 | Ogilvie Raceway - Ogilvie, MN Saturday Night Racing featuring the Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jon Tollakson (WISSOTA Late Model) | 3rd | - | - | 10th |
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| 6/8/2023 | KRA Speedway - Willmar, MN WISSOTA Late Model Challenge Series Night WISSOTA Late Model: Wissota Late Model Challenge Series Dirt Late Models, Pure Stock, WISSOTA Modifieds, WISSOTA Street Stock | Results | | Jon Tollakson (WISSOTA Late Model) | 2nd | - | - | 6th |
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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 | | Jon Tollakson (WISSOTA Late Model) | 7th | - | - | 19th (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 | | Jon Tollakson (WISSOTA Late Model) | 9th (DNF) | - | - | 24th (DNF) |
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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 | | Jon Tollakson (Dirt Late Models) | 8th | - | 9th | - |
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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 | | Jon Tollakson (Dirt Late Models) | 1st | - | - | 24th (DNF) |
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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 | | Jon Tollakson (Dirt Late Models) | 7th | - | 6th | - |
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| 6/23/2023 | Fiesta City Speedway - Montevideo, MN Midwest Modified Special Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jon Tollakson (WISSOTA Late Model) | 3rd | - | - | 2nd |
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| 6/30/2023 | Fiesta City Speedway - Montevideo, MN Regular Race Night - Meet the Drivers Night Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jon Tollakson (WISSOTA Late Model) | 4th | - | - | 3rd |
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| 7/7/2023 | Fiesta City Speedway - Montevideo, MN Super Stock Special Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jon Tollakson (WISSOTA Late Model) | 6th (DNF) | - | - | 4th |
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| 7/14/2023 | Fiesta City Speedway - Montevideo, MN Regular Race Night w/ Limited Late Models Factory Stocks, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jon Tollakson (WISSOTA Late Model) | 1st | - | - | 6th |
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| 7/17/2023 | Ogilvie Raceway - Ogilvie, MN XR Northern Storm WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds | Results | | Jon Tollakson (WISSOTA Late Model) | 7th | - | 8th | 17th |
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| 7/21/2023 | Fiesta City Speedway - Montevideo, MN Dirt Race Central Street Stock Tour WISSOTA Street Stock: Street Stock Tour Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jon Tollakson (WISSOTA Late Model) | 1st | - | - | 4th |
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| 7/26/2023 | Fiesta City Speedway - Montevideo, MN Fair Races Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jon Tollakson (WISSOTA Late Model) | 4th | - | - | 4th |
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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 | | Jon Tollakson (Dirt Late Models) | 3rd | - | - | 20th (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 | | Jon Tollakson (Dirt Late Models) | 3rd | - | 1st | 16th |
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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 | | Jon Tollakson (Dirt Late Models) | 5th | - | 2nd | 23rd (DNF) |
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| 8/18/2023 | Fiesta City Speedway - Montevideo, MN Late Model Special - Day 1 Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jon Tollakson (WISSOTA Late Model) | 6th | - | - | 9th |
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| 8/19/2023 | Fiesta City Speedway - Montevideo, MN Late Model Special Day 2 Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jon Tollakson (WISSOTA Late Model) | 5th | - | - | 11th |
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| 8/25/2023 | Fiesta City Speedway - Montevideo, MN Season Championship Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jon Tollakson (WISSOTA Late Model) | 3rd | - | - | 4th |
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| 9/7/2023 | River Cities Speedway - Grand Forks, ND Prelude to the Johnny - NLRA Championship Open Dirt Karts, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, Flat Jr. 2 Clone Heavy | Results | | Jon Tollakson (WISSOTA Late Model) | 5th | - | 6th | - |
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| 9/8/2023 | River Cities Speedway - Grand Forks, ND John Seitz Memorial Night 1 Open Dirt Karts, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, Flat Jr. 2 Clone Heavy | Results | | Jon Tollakson (WISSOTA Late Model) | 9th (DNF) | - | 18th (DNF) | - |
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| 9/13/2023 | I-94 Speedway - Fergus Falls, MN Speedway Motors WISSOTA 100 Night 1 WISSOTA Late Model: Wissota Late Model Challenge Series DIRTcar UMP Modifieds, A Modifieds, Open Dirt Karts, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, Flat Jr. 2 Clone Heavy | Results | | Jon Tollakson (WISSOTA Late Model) | 7th | - | 10th | - |
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| 9/14/2023 | I-94 Speedway - Fergus Falls, MN Speedway Motors WISSOTA 100 Night 2 DIRTcar UMP Modifieds, Open Dirt Karts, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, Flat Jr. 2 Clone Heavy | Results | | Jon Tollakson (WISSOTA Late Model) | 3rd | - | - | 8th |
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| 9/16/2023 | I-94 Speedway - Fergus Falls, MN Speedway Motors WISSOTA 100 Champion Night DIRTcar UMP Modifieds, A Modifieds, Open Dirt Karts, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, Flat Jr. 2 Clone Heavy | Results | | Jon Tollakson (WISSOTA Late Model) | - | - | - | 24th (DNF) |
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