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| 1/13/2021 | Arizona Speedway - Queen Creek, AZ Dirt Super Late Models, A Modifieds, B Modifieds | Results | | Matt Gilbertson (A Modifieds) | 11th | - | 22nd | - |
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| 5/1/2021 | Miller Central Speedway - Miller, SD Season Opener- Sponsored by Quoin Financial Bank Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Matt Gilbertson (WISSOTA Modifieds) | 1st | - | - | 1st |
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| 5/7/2021 | Fiesta City Speedway - Montevideo, MN Season Opener Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Matt Gilbertson (WISSOTA Modifieds) | 1st | - | - | 3rd |
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| 5/14/2021 | Fiesta City Speedway - Montevideo, MN Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Rain Out |
| 5/21/2021 | Fiesta City Speedway - Montevideo, MN Hornet Special Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Matt Gilbertson (WISSOTA Modifieds) | 8th (DNF) | - | - | 5th |
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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: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: Traditional Sprint Car Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Matt Gilbertson (WISSOTA Modifieds) | 3rd | - | - | DNS |
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| 5/30/2021 | Casino Speedway - Watertown, SD Casino Speedway Memoral Hornets, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock | Results | | Matt Gilbertson (WISSOTA Modifieds) | 3rd | - | - | 5th |
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| 6/4/2021 | Fiesta City Speedway - Montevideo, MN Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Hornet | Results | | Matt Gilbertson (WISSOTA Modifieds) | 3rd | - | - | 1st |
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| 6/11/2021 | Fiesta City Speedway - Montevideo, MN Race of Champions Night Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Matt Gilbertson (WISSOTA Modifieds) | 1st | - | - | 1st |
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| 6/12/2021 | North Central Speedway - Brainerd, MN Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Matt Gilbertson (A Modifieds) | 2nd | - | - | 5th |
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| 6/18/2021 | Fiesta City Speedway - Montevideo, MN Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Matt Gilbertson (WISSOTA Modifieds) | 2nd | - | - | 2nd |
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| 6/24/2021 | Princeton Speedway - Princeton, MN Siercks Memorial Hobby Stocks, A Modifieds, B Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Matt Gilbertson (IMCA Modified) | 7th | - | DNS | - |
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| 6/25/2021 | North Central Speedway - Brainerd, MN 10000 lakes 10k A Modifieds, B Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Matt Gilbertson (IMCA Modified) | 2nd | - | - | 10th |
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| 6/26/2021 | North Central Speedway - Brainerd, MN 10000 lakes 10k IMCA Modified: Land of Ten Thousand Lakes 10K A Modifieds, B Modifieds, IMCA Northern SportMod, IMCA Stock Car | Results | | Matt Gilbertson (IMCA Modified) | 4th | - | 3rd | - |
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| 6/27/2021 | Granite City Motor Park - Sauk Rapids, MN IMCA - $10K to Win! IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Matt Gilbertson (IMCA Modified) | 4th | - | 1st | 22nd (DNF) |
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| 7/4/2021 | Jamestown Speedway - Jamestown, ND Fireworks Spectacular Race Night Semi-Pro Legends, Pure Stock, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Street Stock, Junior Slingshots | Results | | Matt Gilbertson (IMCA Modified) | 4th | - | - | 4th |
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| 7/9/2021 | Fiesta City Speedway - Montevideo, MN Josh Grinager Pure Stock Special Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Matt Gilbertson (WISSOTA Modifieds) | 1st | - | - | 2nd |
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| 7/22/2021 | Norman County Raceway - Ada, MN Advantage RV Mod Tour IMCA Northern SportMod, IMCA Stock Car, WISSOTA Midwest Mods, WISSOTA Modifieds | Results | | Matt Gilbertson (WISSOTA Modifieds) | 1st | - | - | 9th |
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| 7/23/2021 | River Cities Speedway - Grand Forks, ND Big Motor Mania & Hall of Fame Night 410 Sprints - Winged: Northern Outlaw Sprint Association B Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model | Results | | Matt Gilbertson (WISSOTA Modifieds) | 3rd | - | - | 4th |
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| 7/30/2021 | Fiesta City Speedway - Montevideo, MN Fair Races Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Matt Gilbertson (WISSOTA Modifieds) | 1st | - | - | 5th |
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| 8/6/2021 | Fiesta City Speedway - Montevideo, MN Factory Stocks, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Matt Gilbertson (WISSOTA Modifieds) | 3rd | - | - | 3rd |
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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 | | Matt Gilbertson (WISSOTA Modifieds) | 1st | - | - | 1st |
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| 8/14/2021 | Miller Central Speedway - Miller, SD Advantage RV Mod Tour A Modifieds, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Matt Gilbertson (WISSOTA Modifieds) | 1st | - | - | 3rd |
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| 8/15/2021 | Casino Speedway - Watertown, SD ADVANTAGE RV MOD TOUR FINALS WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Matt Gilbertson (WISSOTA Modifieds) | 4th | - | - | 15th (DNF) |
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| 8/21/2021 | Madison Speedway - Madison, MN $1,500 to win at Madison Speedway Dirt Late Models: Tri-State Late Models Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Matt Gilbertson (WISSOTA Modifieds) | 3rd | - | - | 3rd |
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| 8/29/2021 | Casino Speedway - Watertown, SD Sunday Night Rain Date Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Hornet | Results | | Matt Gilbertson (WISSOTA Modifieds) | 7th (DNF) | - | - | DNS |
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| 9/4/2021 | Viking Speedway - Alexandria, MN Labor Day Double Header Sport Compact, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Matt Gilbertson (WISSOTA Modifieds) | 2nd | - | - | 7th |
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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 | | Matt Gilbertson (WISSOTA Modifieds) | 2nd | - | - | 4th |
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| 9/10/2021 | River Cities Speedway - Grand Forks, ND John Seitz Memorial Night 1 & Wayne Anderson Cup Finale 410 Sprints - Winged: Northern Outlaw Sprint Association B Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock | Results | | Matt Gilbertson (WISSOTA Modifieds) | 3rd | - | - | 10th |
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| 9/11/2021 | River Cities Speedway - Grand Forks, ND John Seitz Memorial Night 2 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock | Results | | Matt Gilbertson (WISSOTA Modifieds) | 2nd | - | - | 15th (DNF) |
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| 10/9/2021 | Murray County Speedway - Slayton, MN Hub City Rumble - Repairable Vehicles.com Tri State Late Models Dirt Late Models: Tri-State Late Models Factory Stocks, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Sport Compact | Results | | Matt Gilbertson (A Modifieds) | 9th (DNF) | - | - | 4th |
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