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| 5/21/2021 | Gondik Law Speedway - Superior, WI Friday Night at the Races WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 7th | - | - | 12th |
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| 5/29/2021 | Rice Lake Speedway - Rice Lake, WI Swant Graber presents Structural Buildings WISSOTA Challenge Series (No Mods) plus PS, St S, SS, MWM WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 6th | - | - | 15th |
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| 6/4/2021 | Gondik Law Speedway - Superior, WI Friday Night at the Races WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 7th | - | - | 23rd (DNF) |
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| 6/13/2021 | Proctor Speedway - Proctor, MN King on the Hill Modified Special WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 7th | - | - | 17th (DNF) |
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| 6/25/2021 | Gondik Law Speedway - Superior, WI Limited Sprints - Winged: Upper Midwest Sprint Car Series Vintage Modifieds: Northern Vintage Stockcar Racers 360 Sprints - Non-Winged, 305 Sprints - Non-Winged, Vintage Full Body Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 6th | - | - | 12th |
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| 7/2/2021 | Gondik Law Speedway - Superior, WI 5th Annual Great Lakes Border Battle-Night #1 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 7th | - | 3rd | 18th |
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| 7/3/2021 | Gondik Law Speedway - Superior, WI 5th Annual Great Lakes Border Battle-Night #2 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 4th | - | - | 20th (DNF) |
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| 7/11/2021 | Proctor Speedway - Proctor, MN Military Night presented by Halvor Lines Trucking WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 6th | - | - | 14th |
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| 7/17/2021 | Ogilvie Raceway - Ogilvie, MN Inaugural USMTS Mod Wars A Modifieds: USMTS - United States Modified Touring Series WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Hornet | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 7th | - | 6th | - |
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| 7/18/2021 | Proctor Speedway - Proctor, MN AFCO ROC Qualifier + Vintage Vintage Modifieds: Northern Vintage Stockcar Racers Vintage Full Body Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 6th | - | - | 12th (DNF) |
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| 7/23/2021 | Gondik Law Speedway - Superior, WI Fair Week-Night #2 305 Sprints - Non-Winged, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 5th | - | - | 11th |
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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 | | Evan Checkalski (WISSOTA Midwest Mods) | 8th (DNF) | - | - | 5th |
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| 8/13/2021 | Gondik Law Speedway - Superior, WI National Suicide Prevention Lifeline Night-Pure Stock Special Vintage Modifieds: Northern Vintage Stockcar Racers Vintage Full Body Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 1st | - | - | 12th |
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| 8/15/2021 | Proctor Speedway - Proctor, MN Non-Winged Sprint Car Special + Weekly Racing 360 Sprints - Non-Winged, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 1st | - | - | 11th (DNF) |
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| 8/20/2021 | Gondik Law Speedway - Superior, WI Badger State Hornet Nationals/AFCO Race of Champions/Hall of Fame Night WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 5th | - | - | 8th |
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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 | | Evan Checkalski (WISSOTA Midwest Mods) | 2nd | - | - | 8th |
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| 8/22/2021 | Proctor Speedway - Proctor, MN 70th Anniversary Season Championship WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 1st | - | - | 1st |
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| 9/3/2021 | Grand Rapids Speedway - Grand Rapids, MN Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock | Rain Out |
| 9/4/2021 | Rice Lake Speedway - Rice Lake, WI Holiday Season Finale, $1000 to win Pure Stocks (Increased pay all classes) WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 6th | - | 4th | - |
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| 9/9/2021 | Gondik Law Speedway - Superior, WI Northern Nationals-Night #1 305 Sprints - Non-Winged, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 4th | - | - | 13th |
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| 9/10/2021 | Gondik Law Speedway - Superior, WI Northern Nationals-Night #2 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 3rd | - | - | 11th |
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| 10/1/2021 | ABC Raceway - Ashland, WI Red Clay Classic A Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 6th | - | 1st | - |
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| 10/15/2021 | Gondik Law Speedway - Superior, WI Inaugural Can-Am Clash-Night #1 Fueled by Superior Fuel WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Evan Checkalski (WISSOTA Midwest Mods) | 4th | - | - | 13th |
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