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| 6/5/2020 | Eagle Valley Speedway - Jim Falls, WI 6th Annual Southworth Chevrolet - Tim's Automotive Machine Midwest Mod Special Hornets, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 3rd | - | - | 8th |
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| 6/12/2020 | Dacotah Speedway - Mandan, ND Mandan Dirt Series with WISSOTA Street Stock Tour Hobby Stocks, Semi-Pro Legends, IMCA Modified, IMCA Sport Compact, WISSOTA Street Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 3rd | - | - | 8th |
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| 6/13/2020 | Jamestown Speedway - Jamestown, ND Don Gumke Memorial & 2020 Wissota Street Stock Tour A Modifieds, Street Stocks, Pure Stock, IMCA Modified, WISSOTA Street Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 4th | - | - | 16th |
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| 6/14/2020 | Sheyenne Speedway - Lisbon, ND STREET STOCK TOUR | TOP GUN MW MOD Special | Minn-Kota Legends Tour Pro Legends, Sport Compact, Pure Stock, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 6th | - | - | 13th |
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| 6/20/2020 | Ogilvie Raceway - Ogilvie, MN Season Opener USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | 2nd | - | - | 5th |
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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 | | Kyle Howland (WISSOTA Street Stock) | 2nd | - | - | 1st |
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| 7/10/2020 | I-94 Speedway - Fergus Falls, MN Steffes Street Stock Tour-Minnesota Motors Hornets, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 6th | - | 2nd | 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 | | Kyle Howland (WISSOTA Street Stock) | 1st | - | - | 1st |
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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 | | Kyle Howland (WISSOTA Street Stock) | 3rd | - | - | 1st |
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| 7/21/2020 | Ogilvie Raceway - Ogilvie, MN School Bus Races with Street Stock Tour Special WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 2nd | - | - | 4th |
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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 | | Kyle Howland (WISSOTA Street Stock) | 3rd | - | - | 1st |
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| 7/31/2020 | Eagle Valley Speedway - Jim Falls, WI EDI Nordson, Don Hazelton Memorial Friday Night WISSOTA Auto Racingm with Northern Vintage Racing Hornets, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 4th | - | - | 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 | | Kyle Howland (WISSOTA Street Stock) | 3rd | - | - | 5th |
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| 8/4/2020 | Rice Lake Speedway - Rice Lake, WI 26th Annual Street Stock Little Dream Race-Rain Date August 5th WISSOTA Street Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 4th | - | 2nd | 17th |
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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 | | Kyle Howland (WISSOTA Street Stock) | 1st | - | - | 4th |
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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 | | Kyle Howland (WISSOTA Street Stock) | 2nd | - | - | 1st |
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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 | | Kyle Howland (WISSOTA Street Stock) | 1st | - | - | 2nd |
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| 9/4/2020 | I-94 Speedway - Fergus Falls, MN Season Championship-Sure Step Night Hornets, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 5th | - | - | 7th |
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| 9/11/2020 | Cedar Lake Speedway - New Richmond, WI Sprints Weekend Limited Sprints - Winged: UMSS Winged Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Winged A-Class, Street Stocks, 305 Sprints - Non-Winged | Results | | Kyle Howland (Street Stocks) | 2nd | - | - | 6th |
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