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| 5/20/2023 | Hibbing Raceway - Hibbing, MN Season Opener WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock, WISSOTA Hornet | Results | | Dane Olson (WISSOTA Midwest Mods) | 8th | - | - | 17th |
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| 5/21/2023 | Proctor Speedway - Proctor, MN Sunday Night Showdown WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Dane Olson (WISSOTA Midwest Mods) | 3rd | - | - | 12th (DNF) |
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| 6/15/2023 | Grand Rapids Speedway - Grand Rapids, MN Fast Lane Motorsports Northland Super Stock Series WISSOTA Super Stock: Fast Lane Motorsports Northland Super Stock Series Non-Winged Sprints, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Dane Olson (WISSOTA Midwest Mods) | 5th | - | - | 4th |
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| 6/22/2023 | Norman County Raceway - Ada, MN Norman County Raceway WISSOTA Midwest Mods: Rebel Midwest Mod Tour IMCA RaceSaver Sprint Car, WISSOTA Late Model | Results | | Dane Olson (WISSOTA Midwest Mods) | 5th | - | - | 16th |
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| 6/29/2023 | ABC Raceway - Ashland, WI White River Ag Products Farm Stock Special Dirt 6-cyl Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock | Rain Out |
| 6/30/2023 | Gondik Law Speedway - Superior, WI Great Lakes Border Battle-Night #1/Gondik Law Late Model Series WISSOTA Late Model: KME Late Model Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Dane Olson (WISSOTA Midwest Mods) | 6th | - | 7th | - |
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| 7/1/2023 | Gondik Law Speedway - Superior, WI Great Lakes Border Battle-Night #2/Gondik Law Late Model Series WISSOTA Late Model: KME Late Model Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Super Stock, WISSOTA Hornet | Results | | Dane Olson (WISSOTA Midwest Mods) | 8th | - | 4th | 21st (DNF) |
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| 7/8/2023 | Emo Speedway - Emo, ON Saturday Night Racing! Street Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds | Results | | Dane Olson (WISSOTA Midwest Mods) | 2nd | - | - | 5th |
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| 7/22/2023 | Emo Speedway - Emo, ON Saturday Night Racing Street Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds | Results | | Dane Olson (WISSOTA Midwest Mods) | 1st | - | - | 1st |
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| 8/4/2023 | Emo Speedway - Emo, ON Friday Night Racing! Street Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds | Results | | Dane Olson (WISSOTA Midwest Mods) | 3rd | - | - | 16th (DNF) |
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| 9/1/2023 | Grand Rapids Speedway - Grand Rapids, MN Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Dane Olson (WISSOTA Midwest Mods) | 2nd | - | - | 9th |
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| 9/2/2023 | Hibbing Raceway - Hibbing, MN Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Super Stock, WISSOTA Hornet | Results | | Dane Olson (WISSOTA Midwest Mods) | 4th | - | 4th | - |
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| 9/14/2023 | Cedar Lake Speedway - New Richmond, WI Legendary 100 Day 1 Limited Sprints - Winged, A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Pure Stock, USRA Late Models | Results | | Dane Olson (Limited Sprints - Winged) | - | - | - | - | | Dane Olson (A Modifieds) | - | - | - | - | | Dane Olson (Midwest Modifieds) | - | - | - | 9th |
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| 9/15/2023 | Cedar Lake Speedway - New Richmond, WI Legendary 100 Day 2 Limited Sprints - Winged, A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Pure Stock, USRA Late Models | Results | | Dane Olson (Midwest Modifieds) | - | - | - | - |
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| 9/16/2023 | Cedar Lake Speedway - New Richmond, WI Legendary 100 Day 3 / Features Limited Sprints - Winged, A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Pure Stock, USRA Late Models | Results | | Dane Olson (Midwest Modifieds) | - | - | 4th | - |
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