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| 5/21/2020 | Gondik Law Speedway - Superior, WI 15th Annual Wehrs Machine Minnesota Modified Nationals driven by Boston Trucking-Night #1 USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Rachel Boston (WISSOTA Hornet) | 6th | - | - | 14th |
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| 5/22/2020 | Gondik Law Speedway - Superior, WI 15th Annual Wehrs Machine Minnesota Modified Nationals driven by Boston Trucking-Night #2 USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Rachel Boston (WISSOTA Hornet) | 7th | - | - | 19th |
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| 5/29/2020 | Gondik Law Speedway - Superior, WI Rescheduled 59th Season Opener USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Rachel Boston (WISSOTA Hornet) | 7th | - | - | 17th |
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| 6/12/2020 | Gondik Law Speedway - Superior, WI Friday Night at the Races DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Rachel Boston (WISSOTA Hornet) | 8th | - | - | 17th |
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| 6/27/2020 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Rachel Boston (WISSOTA Hornet) | 7th | - | - | 20th (DNF) |
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| 7/11/2020 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout with Fireworks Spectacular USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Rachel Boston (WISSOTA Hornet) | 8th (DNF) | - | - | 23rd (DNF) |
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| 7/24/2020 | Gondik Law Speedway - Superior, WI Fair Week-Night #2/Fast Lane Motorsports Northland Super Stock Series WISSOTA Super Stock: Fast Lane Motorsports Northland Super Stock Series WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Rachel Boston (WISSOTA Hornet) | 8th | - | - | 14th |
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| 7/25/2020 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout with Mod Four Spotlight USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Rachel Boston (WISSOTA Hornet) | 6th | - | - | 10th |
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| 8/1/2020 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout Fast Lane Super Stock Series WISSOTA Super Stock: Fast Lane Motorsports Northland Super Stock Series WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Rachel Boston (WISSOTA Hornet) | 4th | - | - | 11th |
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| 8/15/2020 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Rachel Boston (WISSOTA Hornet) | 7th | - | - | 23rd (DNF) |
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| 8/22/2020 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Rachel Boston (WISSOTA Hornet) | 4th | - | - | 10th |
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| 8/29/2020 | Ogilvie Raceway - Ogilvie, MN Track Championship w/ Wissota Late Model USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Rachel Boston (WISSOTA Hornet) | 4th | - | - | 12th |
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| 9/9/2020 | Gondik Law Speedway - Superior, WI Showdown in Souptown/King or Queen of the Hill presented by XR/Practice Stock Cars, A Modifieds, B Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Sport Compact, Super Stocks, Pure Stock | Results | | Rachel Boston (Sport Compact) | - | - | - | - |
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| 9/10/2020 | Gondik Law Speedway - Superior, WI Northern Nationals 305 Sprints - Non-Winged, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Rachel Boston (WISSOTA Hornet) | 4th | - | - | 10th |
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| 9/17/2020 | Cedar Lake Speedway - New Richmond, WI 15th Annual Legendary 100 Day 1 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods | Results | | Rachel Boston (Pony Stock) | - | - | - | 16th |
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| 9/18/2020 | Cedar Lake Speedway - New Richmond, WI 15th Annual Legendary 100 Day 2 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods | Results | | Rachel Boston (Pony Stock) | - | - | - | 11th |
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| 9/19/2020 | Cedar Lake Speedway - New Richmond, WI 15th Annual Legendary 100 Day 3 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods | Results | | Rachel Boston (Pony Stock) | - | - | - | 10th |
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| 10/9/2020 | Ogilvie Raceway - Ogilvie, MN 17th Annual MTH Fall Classic presented by FYE Motorsports Dirt Late Models, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Rachel Boston (WISSOTA Hornet) | 6th | - | - | - |
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| 10/10/2020 | Ogilvie Raceway - Ogilvie, MN 17th Annual MTH Fall Classic presented by FYE Motorsports Dirt Late Models, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Rachel Boston (WISSOTA Hornet) | - | - | 1st | 24th (DNF) |
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