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| 6/13/2020 | Deer Creek Speedway - Spring Valley, MN School Bus Races-Mascot Night-Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jacob Bennett (WISSOTA Street Stock) | 5th | - | - | 14th |
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| 6/27/2020 | Deer Creek Speedway - Spring Valley, MN Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jacob Bennett (WISSOTA Street Stock) | 6th | - | - | 16th |
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| 7/3/2020 | Chateau Speedway - Lansing, MN Season Opener USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jacob Bennett (WISSOTA Street Stock) | 9th | - | - | 16th |
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| 7/10/2020 | Chateau Speedway - Lansing, MN Weekly Racing USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jacob Bennett (WISSOTA Street Stock) | 5th | - | - | 11th |
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| 7/17/2020 | Chateau Speedway - Lansing, MN UMSS Traditional Non Wing Sprints 360 Sprints - Non-Winged, Pure Stock, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jacob Bennett (WISSOTA Street Stock) | 7th | - | - | 9th |
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| 7/18/2020 | Deer Creek Speedway - Spring Valley, MN Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jacob Bennett (WISSOTA Street Stock) | 7th | - | - | 13th |
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| 7/25/2020 | Deer Creek Speedway - Spring Valley, MN Driver Recognition-Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jacob Bennett (WISSOTA Street Stock) | 7th | - | - | 14th |
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| 7/31/2020 | Chateau Speedway - Lansing, MN Weekly Racing USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jacob Bennett (WISSOTA Street Stock) | 7th | - | - | 11th |
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| 8/7/2020 | Chateau Speedway - Lansing, MN Traditional Non Wing Sprints - Fireworks 360 Sprints - Non-Winged, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Jacob Bennett (WISSOTA Street Stock) | 6th | - | - | 10th |
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| 8/8/2020 | Deer Creek Speedway - Spring Valley, MN WISSOTA ROC-Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Rain Out |
| 8/15/2020 | Deer Creek Speedway - Spring Valley, MN Veterans Night-Points Race USRA B-Mods, USRA Modifieds, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jacob Bennett (WISSOTA Street Stock) | 6th | - | - | 11th |
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| 8/22/2020 | Deer Creek Speedway - Spring Valley, MN First Responders Night USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jacob Bennett (WISSOTA Street Stock) | 7th | - | - | 11th (DNF) |
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