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| 4/30/2021 | Dacotah Speedway - Mandan, ND Dacotah Speedway Season Opener Hobby Stocks, Semi-Pro Legends, Pro Legends, IMCA Modified, IMCA Sport Compact, WISSOTA Street Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 2nd | - | - | 12th |
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| 5/1/2021 | Southwest Speedway - Dickinson, ND Season Opener Hobby Stocks, Semi-Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Ivan Sailer (Semi-Pro Legends) | 2nd | - | - | 8th |
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| 5/7/2021 | Dacotah Speedway - Mandan, ND Mandan Dirt Series + 2020 Awards Night Hobby Stocks, Semi-Pro Legends, Pro Legends, IMCA Modified, IMCA Sport Compact, WISSOTA Street Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 2nd | - | - | 9th |
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| 5/14/2021 | Dacotah Speedway - Mandan, ND Mandan Dirt Series Hobby Stocks, Semi-Pro Legends, Pro Legends, IMCA Modified, IMCA Sport Compact, WISSOTA Street Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 2nd | - | - | 10th |
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| 5/15/2021 | Southwest Speedway - Dickinson, ND Regular Night Hobby Stocks, Semi-Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Ivan Sailer (Semi-Pro Legends) | 1st | - | - | 7th |
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| 5/21/2021 | Dacotah Speedway - Mandan, ND Mandan Dirt Series Hobby Stocks, Semi-Pro Legends, Pro Legends, IMCA Modified, IMCA Sport Compact, WISSOTA Street Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 4th | - | - | 25th (DNF) |
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| 5/28/2021 | Dacotah Speedway - Mandan, ND Military Appreciation Night + Mandan Dirt Series Hobby Stocks, Semi-Pro Legends, Pro Legends, IMCA Modified, IMCA Sport Compact, WISSOTA Street Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 2nd | - | - | 8th |
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| 5/29/2021 | Jamestown Speedway - Jamestown, ND Saturday Night Thunder & Armed Forces Night Semi-Pro Legends, Pure Stock, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Street Stock, Junior Slingshots | Rain Out |
| 6/3/2021 | Tri County Speedway - Wishek, ND 2nd Race Hobby Stocks, Young Lions Legends, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Ivan Sailer (Young Lions Legends) | 1st | - | - | 2nd |
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| 6/4/2021 | Dacotah Speedway - Mandan, ND Ironman 100 - Night 1 Semi-Pro Legends, IMCA Modified, WISSOTA Street Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 1st | - | - | 9th |
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| 6/5/2021 | Southwest Speedway - Dickinson, ND Midwest Mashup Hobby Stocks, Semi-Pro Legends, IMCA Stock Car | Results | | Ivan Sailer (Semi-Pro Legends) | 2nd | - | - | 3rd |
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| 6/9/2021 | McLean County Speedway - Underwood, ND Mclean County Speedway Tougher Than Dirt Tour Night IMCA Northern SportMod: Tougher Than Dirt Tour Hobby Stocks, Street Stocks, Semi-Pro Legends, Generic 1, IMCA Hobby Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 2nd | - | - | 4th |
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| 6/11/2021 | Dacotah Speedway - Mandan, ND Mandan Dirt Series Hobby Stocks, Semi-Pro Legends, Pro Legends, IMCA Modified, IMCA Sport Compact, WISSOTA Street Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 4th | - | - | 8th |
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| 6/12/2021 | Southwest Speedway - Dickinson, ND Southwest Speedway Tougher Than Dirt Tour Night IMCA Northern SportMod: Tougher Than Dirt Tour Hobby Stocks, Semi-Pro Legends, IMCA Modified, IMCA Stock Car, IMCA Hobby Stock, Junior Slingshots | Results | | Ivan Sailer (Semi-Pro Legends) | 2nd | - | - | 7th |
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| 6/18/2021 | Dacotah Speedway - Mandan, ND Mandan Dirt Series Hobby Stocks, Semi-Pro Legends, Pro Legends, IMCA Modified, IMCA Sport Compact, WISSOTA Street Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 2nd | - | - | 3rd |
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| 6/19/2021 | Jamestown Speedway - Jamestown, ND JRMC Night & REBEL WISSOTA MW Modified Tour Semi-Pro Legends, Pure Stock, IMCA Modified, WISSOTA Midwest Mods, Junior Slingshots | Results | | Ivan Sailer (Semi-Pro Legends) | 5th | - | - | 6th |
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| 6/25/2021 | McLean County Speedway - Underwood, ND Mid-Summer Chaos sponsored by Dakota West Credit Union Non-Winged Sprints, Semi-Pro Legends, Generic 1, Sport Compact | Results | | Ivan Sailer (Semi-Pro Legends) | 3rd | - | - | 4th |
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| 6/26/2021 | Southwest Speedway - Dickinson, ND Richard Jordan Memorial Hobby Stocks, Semi-Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Ivan Sailer (Semi-Pro Legends) | 3rd | - | - | 3rd |
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| 7/2/2021 | McLean County Speedway - Underwood, ND A-Mod Showdown 4.0 sponsored by Quality Dirtworks A Modifieds, B Modifieds, Street Stocks, Non-Winged Sprints, Semi-Pro Legends, Generic 1, IMCA Northern SportMod, IMCA Hobby Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 1st | - | - | 6th |
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| 7/3/2021 | Southwest Speedway - Dickinson, ND Roughrider Days Race Hobby Stocks, Semi-Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Ivan Sailer (Semi-Pro Legends) | 3rd | - | - | 4th |
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| 7/8/2021 | Tri County Speedway - Wishek, ND Fair race Hobby Stocks, Young Lions Legends, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Ivan Sailer (Young Lions Legends) | 4th | - | - | 7th |
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| 7/15/2021 | Dacotah Speedway - Mandan, ND Dakota Classic Modified Tour - Championship Night IMCA Modified: Dakota Classic Modified Tour Semi-Pro Legends, IMCA Stock Car | Results | | Ivan Sailer (Semi-Pro Legends) | 3rd | - | - | 6th |
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| 7/17/2021 | Jamestown Speedway - Jamestown, ND Race of Champion Qualifier, INEX Legends Special, & Kids Night Semi-Pro Legends, Pure Stock, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Street Stock, Junior Slingshots | Results | | Ivan Sailer (Semi-Pro Legends) | 1st | - | - | 9th |
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| 7/22/2021 | Tri County Speedway - Wishek, ND 7th Race Hobby Stocks, Young Lions Legends, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Ivan Sailer (Young Lions Legends) | 4th | - | - | 8th |
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| 7/23/2021 | Dacotah Speedway - Mandan, ND Mandan Dirt Series + Race of Champions Qualifier Hobby Stocks, Semi-Pro Legends, Pro Legends, IMCA Modified, IMCA Sport Compact, WISSOTA Street Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 3rd | - | - | 22nd (DNF) |
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| 7/30/2021 | Dacotah Speedway - Mandan, ND ND Governors Cup Auto Races - Night 1 410 Sprints - Winged: Northern Outlaw Sprint Association Hobby Stocks, Semi-Pro Legends, IMCA Modified, IMCA Sport Compact, WISSOTA Street Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 7th | - | 2nd | 17th |
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| 7/31/2021 | Dacotah Speedway - Mandan, ND ND Governors Cup Auto Races - Night 2 410 Sprints - Winged: Northern Outlaw Sprint Association Hobby Stocks, Semi-Pro Legends, IMCA Modified, IMCA Sport Compact, WISSOTA Street Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 5th | - | - | 16th |
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| 8/5/2021 | Tri County Speedway - Wishek, ND Championship night(Rain Makeup Date) Hobby Stocks, Young Lions Legends, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Ivan Sailer (Young Lions Legends) | 3rd | - | - | 8th |
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| 8/6/2021 | McLean County Speedway - Underwood, ND Kid's Night/Championship Night sponsored by Rusted Rail B Modifieds, Street Stocks, Non-Winged Sprints, Semi-Pro Legends, Generic 1, IMCA Northern SportMod, IMCA Hobby Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 3rd | - | - | 11th |
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| 8/7/2021 | Southwest Speedway - Dickinson, ND Regular Night Hobby Stocks, Semi-Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Ivan Sailer (Semi-Pro Legends) | 6th | - | - | 3rd |
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| 8/13/2021 | Dacotah Speedway - Mandan, ND Mandan Dirt Series Hobby Stocks, Semi-Pro Legends, IMCA Modified, IMCA Sport Compact, WISSOTA Street Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 6th | - | - | 7th |
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| 8/14/2021 | Jamestown Speedway - Jamestown, ND Saturday Night Thunder Semi-Pro Legends, Pure Stock, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Street Stock, Junior Slingshots | Results | | Ivan Sailer (Semi-Pro Legends) | 3rd | - | - | 11th |
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| 8/21/2021 | Southwest Speedway - Dickinson, ND Season Championship Hobby Stocks, Semi-Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Ivan Sailer (Semi-Pro Legends) | 3rd | - | - | 10th |
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| 8/27/2021 | Dacotah Speedway - Mandan, ND Championship Night + Drive to Survive Night Hobby Stocks, Semi-Pro Legends, IMCA Modified, IMCA Sport Compact, WISSOTA Street Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 2nd | - | - | 14th |
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| 8/28/2021 | Jamestown Speedway - Jamestown, ND Season Championship Night & Kuchen Invitational Semi-Pro Legends, Pure Stock, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Street Stock, Junior Slingshots | Results | | Ivan Sailer (Semi-Pro Legends) | 6th | - | - | 16th |
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| 9/10/2021 | Tri County Speedway - Wishek, ND Saurkraut Day 1 Hobby Stocks, Young Lions Legends, Sport Compact, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Ivan Sailer (Young Lions Legends) | 3rd | - | - | 6th |
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| 9/11/2021 | Tri County Speedway - Wishek, ND Saurkraut Day 2 Hobby Stocks, Young Lions Legends, Sport Compact, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Ivan Sailer (Young Lions Legends) | 2nd | - | - | 23rd |
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| 9/24/2021 | Jamestown Speedway - Jamestown, ND 50th Annual Jamestown Stock Car Stampede B Modifieds, Semi-Pro Legends, Pure Stock, IMCA Modified, IMCA Northern SportMod, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Street Stock, Junior Slingshots | Results | | Ivan Sailer (Semi-Pro Legends) | 5th | - | - | 11th |
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| 9/25/2021 | Jamestown Speedway - Jamestown, ND 50th Annual Jamestown Stock Car Stampede B Modifieds, Semi-Pro Legends, Pure Stock, IMCA Modified, IMCA Northern SportMod, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Street Stock, Junior Slingshots | Results | | Ivan Sailer (Semi-Pro Legends) | 2nd | - | - | 17th |
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| 10/1/2021 | Dacotah Speedway - Mandan, ND Oktoberfest - Night 1 Hobby Stocks, Non-Winged Sprints, Semi-Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact, WISSOTA Street Stock | Results | | Ivan Sailer (Semi-Pro Legends) | 4th | - | - | - |
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| 10/2/2021 | Dacotah Speedway - Mandan, ND Oktoberfest - Night 2 Hobby Stocks, Non-Winged Sprints, Semi-Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact, WISSOTA Street Stock | Results | | Ivan Sailer (Semi-Pro Legends) | - | - | - | 11th |
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