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| 5/12/2023 | Outagamie Speedway - Seymour, WI The Wisconsin Dirt Legends make a visit to Outagamie Speedway Pro Legends: Midwest Legends Dirt Series Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Jerry Vanderloop (IMCA Northern SportMod) | 7th | - | 5th | - |
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| 5/13/2023 | Shawano Speedway - Shawano, WI Stock Cars, A Modifieds, B Modifieds, Dirt Late Models, Dirt 4 cyl Modifieds | Results | | Jerry Vanderloop (B Modifieds) | 3rd | - | - | 7th |
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| 5/19/2023 | Outagamie Speedway - Seymour, WI Old Glory Honor Flight & Armed Forces Night at Outagamie Speedway Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Jerry Vanderloop (IMCA Northern SportMod) | 1st | - | - | 15th |
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| 5/20/2023 | Shawano Speedway - Shawano, WI Mighty 4 Special Stock Cars, A Modifieds, B Modifieds, Dirt Late Models, Dirt 4 cyl Modifieds | Results | | Jerry Vanderloop (B Modifieds) | 2nd | - | - | 2nd |
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| 5/26/2023 | Outagamie Speedway - Seymour, WI WABAM Dirt Kings Late Models Salute to Service 30 Dirt Late Models: Dirt Kings Late Model Tour Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Jerry Vanderloop (IMCA Northern SportMod) | 6th | - | 2nd | 16th |
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| 5/27/2023 | Shawano Speedway - Shawano, WI Dirt Kings Tour by Raddant Electric Dirt Late Models: Dirt Kings Late Model Tour Stock Cars, A Modifieds, B Modifieds, Dirt 4 cyl Modifieds | Results | | Jerry Vanderloop (B Modifieds) | 8th | - | - | 12th |
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| 6/2/2023 | Outagamie Speedway - Seymour, WI 6 Divisions of Excitement Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Jerry Vanderloop (IMCA Northern SportMod) | 4th | - | - | 13th |
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| 6/3/2023 | Shawano Speedway - Shawano, WI Hall of Fame Night Stock Cars, A Modifieds, B Modifieds, Dirt Late Models, Dirt 4 cyl Modifieds | Results | | Jerry Vanderloop (B Modifieds) | 4th | - | - | 8th |
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| 6/9/2023 | Outagamie Speedway - Seymour, WI IMCA Stock Cars compete for $1,000 to win Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Jerry Vanderloop (IMCA Northern SportMod) | 9th | - | DNS | - |
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| 6/16/2023 | Outagamie Speedway - Seymour, WI Weekly Racing Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Jerry Vanderloop (IMCA Northern SportMod) | 5th | - | - | 19th (DNF) |
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| 6/17/2023 | Shawano Speedway - Shawano, WI Racing for a Reason - $4000 to win Stock Cars Stock Cars, A Modifieds, B Modifieds, Dirt Late Models, Dirt 4 cyl Modifieds | Results | | Jerry Vanderloop (B Modifieds) | 3rd | - | - | 7th |
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| 6/23/2023 | Outagamie Speedway - Seymour, WI Weekly Racing Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Jerry Vanderloop (IMCA Northern SportMod) | 1st | - | - | 14th |
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| 6/24/2023 | Shawano Speedway - Shawano, WI $1000 to win modifieds special Stock Cars, A Modifieds, B Modifieds, Dirt Late Models, Dirt 4 cyl Modifieds | Results | | Jerry Vanderloop (B Modifieds) | 6th | - | - | 6th |
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| 6/30/2023 | Outagamie Speedway - Seymour, WI Coors Light presents FIREWORKS & Racing at Outagamie Speedway Dirt Late Models: Dirt Kings Late Model Tour Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Jerry Vanderloop (IMCA Northern SportMod) | 3rd | - | - | 8th |
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| 7/1/2023 | Shawano Speedway - Shawano, WI Tribute to the Veterans Stock Cars, A Modifieds, B Modifieds, Dirt Late Models, Dirt 4 cyl Modifieds | Results | | Jerry Vanderloop (B Modifieds) | 4th | - | - | 4th |
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| 7/7/2023 | Outagamie Speedway - Seymour, WI Weekly Racing Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Jerry Vanderloop (IMCA Northern SportMod) | 5th | - | 1st | 19th (DNF) |
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| 7/8/2023 | Shawano Speedway - Shawano, WI Regular Race Night Stock Cars, A Modifieds, B Modifieds, Dirt Late Models, Dirt 4 cyl Modifieds | Results | | Jerry Vanderloop (B Modifieds) | 4th | - | - | 4th |
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| 7/15/2023 | Shawano Speedway - Shawano, WI Halloween on the Half Mile Stock Cars, A Modifieds, B Modifieds, Dirt Late Models, Dirt 4 cyl Modifieds | Results | | Jerry Vanderloop (B Modifieds) | 4th | - | - | 7th |
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| 7/22/2023 | Shawano Speedway - Shawano, WI $3000 to win IMCA Modified Special Stock Cars, A Modifieds, B Modifieds, Dirt Late Models, Dirt 4 cyl Modifieds | Results | | Jerry Vanderloop (B Modifieds) | 4th | - | - | 11th |
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| 8/4/2023 | Outagamie Speedway - Seymour, WI $500 to win IMCA Sport Compacts Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Jerry Vanderloop (IMCA Northern SportMod) | 6th | - | 2nd | 17th |
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| 8/5/2023 | Shawano Speedway - Shawano, WI Back to the school Stock Cars, A Modifieds, B Modifieds, Dirt Late Models, Dirt 4 cyl Modifieds | Results | | Jerry Vanderloop (B Modifieds) | 3rd | - | - | 6th |
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| 8/12/2023 | Shawano Speedway - Shawano, WI Retro Night by Prime Powersports Stock Cars, A Modifieds, B Modifieds, Dirt Late Models, Dirt 4 cyl Modifieds | Results | | Jerry Vanderloop (B Modifieds) | 2nd | - | - | 7th |
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| 8/15/2023 | 141 Speedway - Maribel, WI East Central Coin Captain of the Creek V for IMCA SportMods / $1,000 Blue Race Modifieds / $500 G N Stock Cars, IMCA Modified, IMCA Northern SportMod | Results | | Jerry Vanderloop (IMCA Northern SportMod) | 9th | - | - | - |
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| 8/16/2023 | 141 Speedway - Maribel, WI East Central Coin Captain of the Creek V $10,000 IMCA SportMods / $500 Stock Cars / $500 Sp Compact Sport Compact, IMCA Northern SportMod, IMCA Stock Car | Results | | Jerry Vanderloop (IMCA Northern SportMod) | 7th | - | - | - |
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| 8/19/2023 | Shawano Speedway - Shawano, WI Fan Appreciation Night - $3000 to win Sport Mods Stock Cars, A Modifieds, B Modifieds, Dirt Late Models, Dirt 4 cyl Modifieds | Results | | Jerry Vanderloop (B Modifieds) | 1st | - | - | 9th |
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| 8/26/2023 | Shawano Speedway - Shawano, WI Regular Race Night Dirt Late Models: Dirt Kings Late Model Tour Stock Cars, A Modifieds, B Modifieds, Dirt 4 cyl Modifieds | Results | | Jerry Vanderloop (B Modifieds) | 2nd | - | - | 4th |
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| 9/2/2023 | Shawano Speedway - Shawano, WI Championship Night Stock Cars, A Modifieds, B Modifieds, Dirt Late Models, Dirt 4 cyl Modifieds | Results | | Jerry Vanderloop (B Modifieds) | 5th | - | - | 14th |
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| 9/30/2023 | Luxy Raceway - Luxemburg, WI Fall Classic Street Stocks, Baby Grand, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Jerry Vanderloop (IMCA Northern SportMod) | 1st | - | - | 7th |
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