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| 5/8/2023 | Clay County Fair Speedway - Spencer, IA Dirt Crown - Stock Car Spring Shootout Stock Cars: Dirt Crown B Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 2nd | - | - | 4th |
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| 5/21/2023 | Clay County Fair Speedway - Spencer, IA The Clay County Classic Night #1 Stock Cars: Dirt Crown IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock | Results | | Tim Rupp (IMCA Stock Car) | 7th | - | - | - |
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| 5/22/2023 | Clay County Fair Speedway - Spencer, IA The Clay County Classic Night #2 Stock Cars: Dirt Crown B Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 2nd | - | - | 19th (DNF) |
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| 5/24/2023 | Buena Vista Raceway - Alta, IA Season Opener Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 3rd | - | - | 3rd |
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| 5/31/2023 | Buena Vista Raceway - Alta, IA Weekly Racing & Racesaver Sprint Cars 305 Sprints - Winged, Street Stocks, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 7th | - | - | 1st |
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| 6/5/2023 | Clay County Fair Speedway - Spencer, IA Cole Millard Memorial IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 1st | - | - | 17th (DNF) |
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| 6/7/2023 | Buena Vista Raceway - Alta, IA Battle at the Beaver Dirt Crown Stock Cars: Dirt Crown Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 1st | - | - | 7th |
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| 6/14/2023 | Buena Vista Raceway - Alta, IA Jimmy Squibb Memorial Race Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 1st | - | - | 1st |
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| 6/21/2023 | Buena Vista Raceway - Alta, IA Weekly Racing Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 3rd | - | - | 2nd |
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| 6/26/2023 | Clay County Fair Speedway - Spencer, IA Midwest Madness Tour IMCA Modified: Midwest Madness Tour A Modifieds, B Modifieds, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 3rd | - | - | 1st |
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| 6/28/2023 | Buena Vista Raceway - Alta, IA Midwest Madness Tour & Kyle Suter Memorial Race IMCA Modified: Midwest Madness Tour A Modifieds, B Modifieds, Street Stocks, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 1st | - | - | 19th (DNF) |
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| 7/15/2023 | Boone Speedway - Boone, IA Saturday Night Series Weekly #14 IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Mod Lite | Results | | Tim Rupp (IMCA Stock Car) | 4th | - | - | 21st (DNF) |
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| 7/19/2023 | Buena Vista Raceway - Alta, IA Weekly Racing Street Stocks, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 3rd | - | - | 3rd |
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| 7/26/2023 | Clay County Fair Speedway - Spencer, IA Salute to Veterans Tour A Modifieds, B Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 5th | - | 2nd | 11th |
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| 8/2/2023 | Buena Vista Raceway - Alta, IA Weekly Racing Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 5th | - | - | 2nd |
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| 8/16/2023 | Buena Vista Raceway - Alta, IA Weekly Racing Street Stocks, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 3rd | - | - | 10th (DNF) |
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| 8/23/2023 | Buena Vista Raceway - Alta, IA Season Championship Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 2nd | - | - | 1st | | Tim Rupp (IMCA Hobby Stock) | - | - | - | - |
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| 9/12/2023 | Clay County Fair Speedway - Spencer, IA 360 Sprints - Winged: ASCS National Dirt Super Late Models: SLMR Late Model Series Midgets, Dirt Late Models, IMCA Stock Car | Results | | Tim Rupp (IMCA Stock Car) | 1st | - | - | 24th (DNF) |
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| 9/13/2023 | Clay County Fair Speedway - Spencer, IA IMCA Blue Ribbon Showdown B Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 3rd | - | - | 19th (DNF) |
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| 9/29/2023 | Park Jefferson International Speedway - Jefferson, SD Iron Cup Dirt Super Late Models, B Modifieds, Dirt Late Models, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 4th | - | - | 8th |
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| 9/30/2023 | Park Jefferson International Speedway - Jefferson, SD Iron Cup Dirt Super Late Models, B Modifieds, Dirt Late Models, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | - | 5th | - | 4th |
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| 10/21/2023 | Park Jefferson International Speedway - Jefferson, SD Charlie Clark Memorial $5022 to win! A Modifieds, B Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tim Rupp (IMCA Stock Car) | 4th | - | - | 16th |
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