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| 6/5/2021 | Gillette Thunder Speedway - Gillette, WY PACK THE STANDS! $ Month Of Money $ Series Finale IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model | Results | | Matthew Drake (WISSOTA Midwest Mods) | 5th | - | - | 13th |
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| 6/12/2021 | Gillette Thunder Speedway - Gillette, WY ASCS Elite North - Non-Wing Sprint Car Tour Non-Winged Sprints, 305 Sprints - Non-Winged, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four | Results | | Matthew Drake (WISSOTA Midwest Mods) | 4th | - | - | 10th |
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| 6/19/2021 | Gillette Thunder Speedway - Gillette, WY WISSOTA Mod 4 Black Jack Special IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model | Results | | Matthew Drake (WISSOTA Midwest Mods) | 3rd | - | - | 9th |
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| 6/20/2021 | Sheridan Speedway - Sheridan, WY Sponsored by A-Line Roofing & Exteriors and Ted's Towing 360 Sprints - Winged, Quarter Midgets, Dirt Mini Trucks, Junior Honda, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Matthew Drake (WISSOTA Midwest Mods) | 6th | - | - | 12th |
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| 6/27/2021 | Sheridan Speedway - Sheridan, WY Mountain States Modified Tour - Night 3 - Sponsored by AlphaGraphics IMCA Modified, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Matthew Drake (WISSOTA Midwest Mods) | 3rd | - | - | 14th |
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| 7/3/2021 | Gillette Thunder Speedway - Gillette, WY IMCA Hobby Stock + Wissota Mod 4 Specials IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model | Results | | Matthew Drake (WISSOTA Midwest Mods) | 4th | 1st | - | 11th |
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| 7/4/2021 | Casper Speedway - Casper, WY Mike Welch Memorial Mod Four Series Stock Cars, Vintage Modifieds, Dwarf, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four | Results | | Matthew Drake (WISSOTA Midwest Mods) | 5th (DNF) | - | - | 11th (DNF) |
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| 7/10/2021 | Gillette Thunder Speedway - Gillette, WY WISSOTA Midwest Mod Border Clash IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model | Results | | Matthew Drake (WISSOTA Midwest Mods) | 5th | - | - | 14th |
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| 7/11/2021 | Sheridan Speedway - Sheridan, WY Race of Champions - Sponsored by Farmer's Co-op and Jim Volk - Kids Bike Races - Quarter Midgets, Junior Honda, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Matthew Drake (WISSOTA Midwest Mods) | 2nd | - | - | 11th (DNF) |
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| 7/16/2021 | Casper Speedway - Casper, WY Wissota Mid West Modified Daniel Dickerson Memorial Stock Cars, Vintage Modifieds, Dwarf, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four | Results | | Matthew Drake (WISSOTA Midwest Mods) | 9th | - | - | 3rd |
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| 7/17/2021 | Gillette Thunder Speedway - Gillette, WY IMCA Modified .38 Special Sport Compact, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model | Results | | Matthew Drake (WISSOTA Midwest Mods) | 4th | - | - | 12th |
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| 7/24/2021 | Gillette Thunder Speedway - Gillette, WY High Plains Late Model Tour Dirt Super Late Models: High Plains Late Models Sport Compact, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four | Results | | Matthew Drake (WISSOTA Midwest Mods) | 4th | - | - | 14th |
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| 7/25/2021 | Sheridan Speedway - Sheridan, WY ASCS Sprint Special - Sponsored by Heartland Kubota 360 Sprints - Winged: ASCS Frontier Region IMCA Modified, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Matthew Drake (WISSOTA Midwest Mods) | 2nd | - | - | 4th |
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| 7/31/2021 | Gillette Thunder Speedway - Gillette, WY Regular Race Sport Compact, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four | Results | | Matthew Drake (WISSOTA Midwest Mods) | 3rd | - | - | 10th |
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| 8/1/2021 | Sheridan Speedway - Sheridan, WY Mini Stock Special - Sponsored Alpine Climate Control and Jack Wood Quarter Midgets, Dirt Mini Trucks, Junior Honda, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Matthew Drake (WISSOTA Midwest Mods) | 2nd | - | - | 10th |
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| 8/7/2021 | Gillette Thunder Speedway - Gillette, WY Regular Race Sport Compact, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model | Results | | Matthew Drake (WISSOTA Midwest Mods) | 3rd | - | - | 11th |
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| 8/13/2021 | Sheridan Speedway - Sheridan, WY I 90 - Night 1 - Sponsored by TireRama and Powder River Power of Sheridan Dirt Mini Trucks, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Matthew Drake (WISSOTA Midwest Mods) | 6th | - | 6th | 16th |
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| 8/14/2021 | Sheridan Speedway - Sheridan, WY I 90 - Night 2 Sponsored by McDonald's Dirt Mini Trucks, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Matthew Drake (WISSOTA Midwest Mods) | 5th | - | 5th | 12th |
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| 8/15/2021 | Sheridan Speedway - Sheridan, WY I 90 - Night 3 Sponsored by Sheridan Homes Quarter Midgets, Dirt Mini Trucks, Junior Honda, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Matthew Drake (WISSOTA Midwest Mods) | 8th (DNF) | - | 11th (DNF) | - |
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| 8/21/2021 | Gillette Thunder Speedway - Gillette, WY Points Championship Night WISSOTA R.O.C Sport Compact, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model | Results | | Matthew Drake (WISSOTA Midwest Mods) | 4th | - | - | 13th |
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| 8/22/2021 | Sheridan Speedway - Sheridan, WY CHAMPIONSHIP NIGHT!!!! -- Sponsored by Rocky Mountain Ambulance Quarter Midgets, Dirt Mini Trucks, Junior Honda, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Matthew Drake (WISSOTA Midwest Mods) | 2nd | - | - | 6th |
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| 9/3/2021 | Gillette Thunder Speedway - Gillette, WY 21ST ANNUAL EAST-WEST CLASH IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Matthew Drake (WISSOTA Midwest Mods) | 2nd | - | - | 6th |
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| 9/4/2021 | Gillette Thunder Speedway - Gillette, WY 21ST ANNUAL EAST-WEST CLASH Sport Compact, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Matthew Drake (WISSOTA Midwest Mods) | 4th | - | - | 19th |
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| 9/5/2021 | Gillette Thunder Speedway - Gillette, WY 21ST ANNUAL EAST-WEST CLASH CHAMPIONSHIP Sport Compact, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Matthew Drake (WISSOTA Midwest Mods) | 5th | DNS | 17th (DNF) | - |
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