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| 5/21/2020 | Gondik Law Speedway - Superior, WI 15th Annual Wehrs Machine Minnesota Modified Nationals driven by Boston Trucking-Night #1 USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 2nd | - | - | 8th |
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| 5/22/2020 | Gondik Law Speedway - Superior, WI 15th Annual Wehrs Machine Minnesota Modified Nationals driven by Boston Trucking-Night #2 USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 6th | - | 4th | 23rd (DNF) |
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| 5/29/2020 | Gondik Law Speedway - Superior, WI Rescheduled 59th Season Opener USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 4th | - | - | 11th |
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| 5/30/2020 | ABC Raceway - Ashland, WI Season Opener presented by the Northern State Bank USRA Modifieds, Dirt 6-cyl Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 6th | - | - | 3rd |
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| 6/4/2020 | Gondik Law Speedway - Superior, WI Gondik Law Speedway Doubleheader Shootout presented by Broking Transport-Night #1 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 8th | - | - | 9th |
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| 6/12/2020 | Gondik Law Speedway - Superior, WI Friday Night at the Races DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 7th | - | - | DNS |
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| 6/19/2020 | Gondik Law Speedway - Superior, WI Rivord Auto & Transmission Repair Night DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 2nd | - | - | 8th |
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| 7/2/2020 | Gondik Law Speedway - Superior, WI 4th Annual Great Lakes Border Battle fueled by Superior Fuel-Night #1 USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 7th | - | 4th | 18th |
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| 7/3/2020 | Gondik Law Speedway - Superior, WI 4th Annual Great Lakes Border Battle fueled by Superior Fuel-Night #2 USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 1st | - | - | 10th |
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| 7/4/2020 | Gondik Law Speedway - Superior, WI 4th Annual Great Lakes Border Battle fueled by Superior Fuel-Night #3 USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 2nd | - | - | 9th |
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| 7/9/2020 | Grand Rapids Speedway - Grand Rapids, MN Thursday Night Thunder Season Opener Non-Winged Sprints, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Rain Out |
| 7/23/2020 | Grand Rapids Speedway - Grand Rapids, MN Fast Lane Northland Super Stock Series Non-Winged Sprints, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 4th | - | - | 5th |
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| 8/1/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #12 A Modifieds, Midwest Modifieds, Super Stocks, USRA Late Models | Results | | Greg Chesley (A Modifieds) | 7th | - | - | 7th |
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| 8/15/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #13 A Modifieds, Midwest Modifieds, 600cc Modifieds, Super Stocks, USRA Modifieds, USRA Late Models | Results | | Greg Chesley (A Modifieds) | 6th | - | - | 17th |
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| 8/21/2020 | Gondik Law Speedway - Superior, WI Inaugural Hornet Nationals/Rescheduled Hall of Fame and National Suicide Prevention Lifeline Night WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 3rd | - | - | 13th (DNF) |
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| 8/28/2020 | Gondik Law Speedway - Superior, WI Season Championship WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 5th | - | - | 9th |
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| 8/29/2020 | Ogilvie Raceway - Ogilvie, MN Track Championship w/ Wissota Late Model USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 1st | - | - | - |
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| 9/3/2020 | ABC Raceway - Ashland, WI Prelude to the Clay USRA Modifieds, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Greg Chesley (WISSOTA Modifieds) | 5th | - | 2nd | 15th |
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| 9/5/2020 | Hibbing Raceway - Hibbing, MN Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 9th | - | 6th | 17th |
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| 9/6/2020 | Hibbing Raceway - Hibbing, MN Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 2nd | - | - | 12th |
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| 9/11/2020 | Gondik Law Speedway - Superior, WI Northern Nationals WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Greg Chesley (WISSOTA Modifieds) | 6th | - | 5th | - |
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| 9/12/2020 | Gondik Law Speedway - Superior, WI Northern Nationals WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Greg Chesley (WISSOTA Modifieds) | 2nd | - | - | 24th (DNF) |
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| 10/2/2020 | ABC Raceway - Ashland, WI Red Clay Classic WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Canceled |
| 10/9/2020 | Ogilvie Raceway - Ogilvie, MN 17th Annual MTH Fall Classic presented by FYE Motorsports Dirt Late Models, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | 2nd | - | - | - |
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| 10/10/2020 | Ogilvie Raceway - Ogilvie, MN 17th Annual MTH Fall Classic presented by FYE Motorsports Dirt Late Models, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Greg Chesley (WISSOTA Modifieds) | - | - | - | 13th |
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