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| 5/30/2020 | Springfield Raceway - Springfield, MO A Modifieds, Midwest Modifieds, Pro Legends, Limited Sport Mod, Pure Stock, USRA B-Mods, Dirt Mini Late Models | Results | | Trenton Simon (A Modifieds) | 6th | - | - | 14th | | Trenton Simon (Pro Legends) | 1st | - | - | 2nd |
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| 6/13/2020 | Springfield Raceway - Springfield, MO A Modifieds, Midwest Modifieds, Pro Legends, Limited Sport Mod, Pure Stock, USRA B-Mods, Dirt Mini Late Models | Results | | Trenton Simon (A Modifieds) | 5th | - | - | 9th | | Trenton Simon (Pro Legends) | 3rd | - | - | 3rd |
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| 6/20/2020 | Springfield Raceway - Springfield, MO Cash Money Late Models A Modifieds, Midwest Modifieds, Dirt Late Models, Pro Legends, Limited Sport Mod, Pure Stock, USRA B-Mods, Dirt Mini Late Models | Results | | Trenton Simon (Pro Legends) | 2nd | - | - | 2nd |
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| 6/27/2020 | Springfield Raceway - Springfield, MO A Modifieds, Midwest Modifieds, Pro Legends, Limited Sport Mod, Pure Stock, USRA B-Mods, Dirt Mini Late Models | Results | | Trenton Simon (Pro Legends) | 2nd | - | - | 1st |
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| 7/18/2020 | Springfield Raceway - Springfield, MO Cash Money Late models A Modifieds, Midwest Modifieds, Dirt Late Models, Pro Legends, Limited Sport Mod, Pure Stock, USRA B-Mods, Dirt Mini Late Models | Results | | Trenton Simon (A Modifieds) | - | - | - | 9th |
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| 7/25/2020 | Springfield Raceway - Springfield, MO A Modifieds, Midwest Modifieds, Pro Legends, Limited Sport Mod, Pure Stock, USRA B-Mods, Dirt Mini Late Models | Results | | Trenton Simon (A Modifieds) | 4th | - | - | 12th | | Trenton Simon (Pro Legends) | 3rd | - | - | 12th |
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| 8/15/2020 | Springfield Raceway - Springfield, MO Cash Money late models A Modifieds, Midwest Modifieds, Dirt Late Models, Pro Legends, Limited Sport Mod, Pure Stock, USRA B-Mods, Dirt Mini Late Models | Results | | Trenton Simon (A Modifieds) | DNS | - | - | 9th | | Trenton Simon (Pro Legends) | DNS | - | - | 3rd |
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| 9/6/2020 | Springfield Raceway - Springfield, MO KTTS OZARKS AREA DIRT TRACK CHAMPIONSHIPS A Modifieds, Midwest Modifieds, Dirt Late Models, Pro Legends, Limited Sport Mod, Pure Stock, USRA B-Mods, Dirt Mini Late Models | Results | | Trenton Simon (Pro Legends) | 2nd | - | - | 16th |
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| 9/19/2020 | Springfield Raceway - Springfield, MO ROUTE 66 SHOWDOWN Stock Cars, A Modifieds, Midwest Modifieds, Dirt Late Models, Limited Sport Mod, USRA B-Mods, Dirt Mini Late Models | Results | | Trenton Simon (A Modifieds) | 5th | - | - | 10th |
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| 9/20/2020 | Springfield Raceway - Springfield, MO ROUTE 66 SHOWDOWN (66 LAPS) Midwest Modifieds, Dirt Late Models, Pro Legends, Pure Stock, USRA B-Mods | Results | | Trenton Simon (Pro Legends) | 1st | - | - | 1st |
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| 10/24/2020 | Springfield Raceway - Springfield, MO Cash Money Late Models/ 5 for 5 Pure Stock Midwest Modifieds, Dirt Late Models, Pro Legends, Limited Sport Mod, Pure Stock, USRA B-Mods | Results | | Trenton Simon (Pro Legends) | 1st | - | - | 12th |
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| 11/7/2020 | Springfield Raceway - Springfield, MO PRELUDE TO TURKEY BOWL XIV Stock Cars, Midwest Modifieds, Dirt Late Models, Pro Legends, Limited Sport Mod, Pure Stock, USRA B-Mods | Results | | Trenton Simon (Pro Legends) | 2nd | - | - | 2nd |
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| 11/27/2020 | Springfield Raceway - Springfield, MO QUALIFYING FOR TURKEY BOWL / TEST N TUNE A Modifieds, Midwest Modifieds, Dirt Late Models, Pro Legends, Limited Sport Mod, Pure Stock, USRA B-Mods, Dirt Mini Late Models | Results | | Trenton Simon (Pro Legends) | 2nd | - | - | - |
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| 11/28/2020 | Springfield Raceway - Springfield, MO TURKEY BOWL XIV A Modifieds, Midwest Modifieds, Dirt Late Models, Pro Legends, Limited Sport Mod, Pure Stock, USRA B-Mods, Dirt Mini Late Models | Results | | Trenton Simon (Pro Legends) | - | - | - | 3rd |
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