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| 4/26/2019 | Ogilvie Raceway - Ogilvie, MN 11th Annual Season Opener Double Header Dirt 4 cyl Modifieds, Super Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | 7th (DNF) | - | - | 8th |
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| 4/27/2019 | Ogilvie Raceway - Ogilvie, MN Double Header Season Opener WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | 4th | - | - | 2nd |
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| 5/4/2019 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout - with Hornet Spotlight 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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| 5/11/2019 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout - Mother's Day Special with Mod Four Spotlight WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Rain Out |
| 6/1/2019 | Ogilvie Raceway - Ogilvie, MN Kids Night "Bike Giveaway" Presented by SPIRE Credit Union 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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| 6/15/2019 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout Father's Day Special & Midwest Modified Spotlight & ROC WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | 3rd | - | - | 1st |
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| 7/3/2019 | Rice Lake Speedway - Rice Lake, WI Firecracker Special DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 4th | - | - | 22nd (DNF) |
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| 7/5/2019 | Chateau Speedway - Lansing, MN Fireworks Spectacular Special USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Rain Out |
| 7/20/2019 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout with Modified spotlight WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | 4th | - | - | 5th |
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| 7/27/2019 | Ogilvie Raceway - Ogilvie, MN Kids Night "Meet the Driver" WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | 1st | - | - | 3rd |
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| 7/30/2019 | Rice Lake Speedway - Rice Lake, WI 25th Annual Street Stock Little Dream WISSOTA Street Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 2nd | - | - | 13th |
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| 8/17/2019 | Ogilvie Raceway - Ogilvie, MN Season Championship WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | 2nd | - | - | 3rd |
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| 8/23/2019 | Ogilvie Raceway - Ogilvie, MN Harvest Cup Special with Wissota Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | 3rd | - | - | 5th |
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| 8/24/2019 | Deer Creek Speedway - Spring Valley, MN Championship Night - Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 5th | - | - | 5th |
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| 9/11/2019 | I-94 Speedway - Fergus Falls, MN WISSOTA 100 - Day 1 Dirt 4 cyl Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 8th | - | - | - |
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| 9/12/2019 | I-94 Speedway - Fergus Falls, MN WISSOTA 100 - Day 2 Dirt 4 cyl Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | - | - | - | - |
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| 9/13/2019 | I-94 Speedway - Fergus Falls, MN WISSOTA 100 - Day 3 WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 11th (DNF) | - | - | - |
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| 9/14/2019 | I-94 Speedway - Fergus Falls, MN WISSOTA 100 FINALE! WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 10th | - | - | - |
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| 10/4/2019 | Ogilvie Raceway - Ogilvie, MN MTH Fall Classic (FYE) Sport Compact, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 2nd | - | - | 5th |
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| 10/18/2019 | Ogilvie Raceway - Ogilvie, MN Topless Nationals A Modifieds, B Modifieds, Street Stocks, Dirt 4 cyl Modifieds, Super Stocks | Results | | Kyle Howland (Street Stocks) | 5th | - | - | - |
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| 10/19/2019 | Ogilvie Raceway - Ogilvie, MN Topless Nationals A Modifieds, B Modifieds, Street Stocks, Dirt 4 cyl Modifieds, Super Stocks | Results | | Kyle Howland (Street Stocks) | - | - | - | 7th |
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