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| 5/8/2021 | Viking Speedway - Alexandria, MN 56th Viking Speedway Season Opener WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Ryan McCleary (WISSOTA Midwest Mods) | 7th | - | - | 12th |
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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: Upper Midwest 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 | | Ryan McCleary (WISSOTA Midwest Mods) | 5th | - | - | 18th |
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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 | | Ryan McCleary (WISSOTA Midwest Mods) | 5th | - | - | 29th (DNF) |
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| 7/24/2021 | Viking Speedway - Alexandria, MN Regular Race Night Plus Short Trackers Sport Compact, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Ryan McCleary (WISSOTA Midwest Mods) | 3rd | - | - | 11th (DNF) |
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| 7/31/2021 | Viking Speedway - Alexandria, MN HALL OF FAME NIGHT - VINTAGE CARS - SHORT TRACKERS Sport Compact, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Ryan McCleary (WISSOTA Midwest Mods) | 5th | - | - | 11th |
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| 8/13/2021 | Fiesta City Speedway - Montevideo, MN Super Stock Special Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Ryan McCleary (WISSOTA Midwest Mods) | 6th | - | - | 6th |
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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 | | Ryan McCleary (WISSOTA Midwest Mods) | 8th | - | - | 13th |
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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 | | Ryan McCleary (WISSOTA Midwest Mods) | 9th | - | - | - |
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| 9/16/2021 | I-94 Speedway - Fergus Falls, MN WISSOTA 100 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Ryan McCleary (WISSOTA Midwest Mods) | 5th | - | - | 23rd |
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| 9/17/2021 | I-94 Speedway - Fergus Falls, MN WISSOTA 100 WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Ryan McCleary (WISSOTA Midwest Mods) | 7th | - | - | - |
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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 | | Ryan McCleary (WISSOTA Midwest Mods) | - | - | - | - |
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