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| 5/20/2023 | Big Sky Speedway - Billings, MT 360 Sprints - Winged: ASCS Frontier Region Semi-Pro Legends, 350 Sprints - Non Winged, IMCA Sport Compact, WISSOTA Street Stock | Results | | Jake Dewitt (350 Sprints - Non Winged) | 4th | - | - | 3rd |
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| 6/17/2023 | Big Sky Speedway - Billings, MT What a LEGENDary night it will be! 360 Sprints - Winged: ASCS Frontier Region Semi-Pro Legends, 350 Sprints - Non Winged, IMCA Modified, IMCA Sport Compact, WISSOTA Midwest Mods | Results | | Jake Dewitt (350 Sprints - Non Winged) | 6th | - | - | 7th (DNF) |
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| 7/7/2023 | Big Sky Speedway - Billings, MT 360 Sprints - Winged: ASCS Frontier Region Semi-Pro Legends, 350 Sprints - Non Winged, WISSOTA Super Stock | Results | | Jake Dewitt (350 Sprints - Non Winged) | 5th | - | - | 7th (DNF) |
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| 7/8/2023 | Big Sky Speedway - Billings, MT 360 Sprints - Winged: ASCS Frontier Region Semi-Pro Legends, 350 Sprints - Non Winged, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jake Dewitt (350 Sprints - Non Winged) | 6th (DNF) | - | - | 3rd |
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| 7/28/2023 | Casper Speedway - Casper, WY 360 Sprints - Winged: ASCS Northern Plains Region Vintage Modifieds, Dwarf, IMCA Hobby Stock, WISSOTA Mod Four | Results | | Jake Dewitt (360 Sprints - Winged) | 6th | - | - | 14th |
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| 8/25/2023 | Big Sky Speedway - Billings, MT Harvey Ostermiller Memorial ($3,000 to win) 360 Sprints - Winged: ASCS Frontier Region Semi-Pro Legends, 350 Sprints - Non Winged, IMCA Modified | Results | | Jake Dewitt (350 Sprints - Non Winged) | 1st | - | - | 3rd |
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| 8/26/2023 | Big Sky Speedway - Billings, MT Harvey Ostermiller Memorial ($12,012 to win) 360 Sprints - Winged: ASCS Frontier Region Semi-Pro Legends, 350 Sprints - Non Winged, IMCA Modified | Results | | Jake Dewitt (350 Sprints - Non Winged) | 8th | - | - | 5th |
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| 9/9/2023 | Big Sky Speedway - Billings, MT 360 Sprints - Winged: ASCS Frontier Region Semi-Pro Legends, 350 Sprints - Non Winged, WISSOTA Midwest Mods | Results | | Jake Dewitt (350 Sprints - Non Winged) | 8th | - | - | 3rd |
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| 10/6/2023 | Big Sky Speedway - Billings, MT Last Weekend of Racing for Big Sky Speedway (Get your FIX before Winter) Semi-Pro Legends, 350 Sprints - Non Winged, IMCA Modified, IMCA Sport Compact, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Jake Dewitt (350 Sprints - Non Winged) | 2nd | - | - | 5th |
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| 10/7/2023 | Big Sky Speedway - Billings, MT Last Weekend of Racing for Big Sky Speedway (Get your FIX before Winter) Semi-Pro Legends, 350 Sprints - Non Winged, IMCA Modified, IMCA Sport Compact, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Jake Dewitt (350 Sprints - Non Winged) | 2nd | - | - | 11th (DNF) |
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