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| 5/15/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout - Armed Forces Night WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | 4th | - | - | 7th |
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| 5/22/2021 | 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 | - | - | 10th (DNF) |
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| 5/28/2021 | I-94 Speedway - Fergus Falls, MN Steffes Street Stock Tour and Traditional Sprint Cars 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Hornets, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 2nd | - | - | 10th |
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| 5/29/2021 | Viking Speedway - Alexandria, MN Memorial Day Double Header Steffes Street Stock Tour and Traditional & Winged Sprint Cars Limited Sprints - Winged: UMSS Winged Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 5th | - | 4th | - |
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| 5/30/2021 | Viking Speedway - Alexandria, MN Memorial Day Double Header Steffes Street Stock Tour and Traditional & Winged Sprint Cars Limited Sprints - Winged: UMSS Winged Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Sprint Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 3rd | - | - | 12th |
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| 6/11/2021 | Brown County Speedway - Aberdeen, SD STREET STOCK TOUR WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 1st | - | - | 11th |
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| 6/12/2021 | Jamestown Speedway - Jamestown, ND 2nd Annual Don Gumke Memorial & Steffes Street Stock Tour Pure Stock, IMCA Modified, WISSOTA Street Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 5th | - | - | 18th |
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| 6/13/2021 | Sheyenne Speedway - Lisbon, ND STEFFES STREET STOCK TOUR Pro Legends, Sport Compact, Pure Stock, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 7th | - | - | 16th |
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| 6/17/2021 | KRA Speedway - Willmar, MN Jeff Isdal Memorial Street Stock Special presented by Deering Sales Inc. Pure Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | 1st | - | - | 8th |
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| 6/18/2021 | River Cities Speedway - Grand Forks, ND Big Al's Street Stock Tour & Premier Racing Series 410 Sprints - Winged: Northern Outlaw Sprint Association B Modifieds, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Street Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 4th | - | - | 16th |
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| 6/19/2021 | Devils Lake Speedway - Crary, ND Cliff Reeves Memorial/Steffes Street Stock Tour Midgets: POWRi Lightning Sprints: POWRi Minn-Kota Lightning Sprints Pure Stock, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 5th | - | - | 22nd (DNF) |
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| 6/26/2021 | 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) | 3rd | - | - | 8th |
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| 7/10/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout with Fireworks Spectacular & Street Stock Special WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | 5th | - | - | 8th |
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| 7/11/2021 | Granite City Motor Park - Sauk Rapids, MN RV Mod Tour and Street Stock Tour A Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | 3rd | - | - | 10th |
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| 7/16/2021 | I-94 Speedway - Fergus Falls, MN Steffes Street Stock Tour plus Super Stock Special Hornets, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Midwest Mods) | - | - | - | - | | Kyle Howland (WISSOTA Street Stock) | 3rd | - | - | 12th |
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| 7/17/2021 | I-94 Speedway - Fergus Falls, MN World of Outlaw Late Models and Steffes Street Stock Special Dirt Super Late Models: World of Outlaws - Late Models WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 6th | - | - | 16th |
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| 7/24/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout with FastLane Motorsports Northland Super Stock Seri WISSOTA Super Stock: Fast Lane Motorsports Northland Super Stock Series WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | 4th | - | - | 1st |
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| 7/30/2021 | I-94 Speedway - Fergus Falls, MN Bob Gierke Memorial A Modifieds, Hornets, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 2nd | - | - | 3rd |
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| 7/31/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout and Bus Races WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | 1st | - | - | 12th (DNF) |
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| 8/14/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout/ ROC race to qualify for the W100 WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | 2nd | - | - | 2nd |
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| 8/15/2021 | Granite City Motor Park - Sauk Rapids, MN Regular Night Races also will be the ROC qualifier race for the WISSOTA 100 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 | - | - | 6th |
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| 8/21/2021 | 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) | 3rd | - | - | 5th |
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| 8/27/2021 | I-94 Speedway - Fergus Falls, MN Race of Champions along Meet and Greet the Drivers, Along with the Viessman Late Model Special Hornets, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 3rd | - | - | 22nd (DNF) |
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| 9/5/2021 | Viking Speedway - Alexandria, MN Labor Day Weekend Night #2 Sport Compact, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 2nd | - | - | 6th |
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| 9/15/2021 | I-94 Speedway - Fergus Falls, MN WISSOTA 100 A Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | 2nd | - | - | 8th |
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| 9/18/2021 | I-94 Speedway - Fergus Falls, MN WISSOTA 100 A Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Howland (WISSOTA Street Stock) | - | - | - | 26th (DNF) |
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| 10/8/2021 | Ogilvie Raceway - Ogilvie, MN Fall Classic presented by FYE Motorsports A Modifieds, USRA Late Models, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | 2nd | - | - | - |
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| 10/9/2021 | Ogilvie Raceway - Ogilvie, MN Fall Classic presented by FYE Motorsports A Modifieds, USRA Late Models, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Kyle Howland (WISSOTA Street Stock) | - | - | - | 6th |
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