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| 1/11/2020 | Arizona Speedway - Queen Creek, AZ Wild West Shootout A Modifieds: Wild West Shootout Dirt Super Late Models, B Modifieds, USRA B-Mods, USRA Modifieds | Results | | Zach Benson (B Modifieds) | 9th | - | 3rd | 15th |
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| 1/12/2020 | Arizona Speedway - Queen Creek, AZ Wild West Shootout A Modifieds: Wild West Shootout Dirt Super Late Models, B Modifieds, USRA B-Mods, USRA Modifieds, IMCA Modified | Results | | Zach Benson (B Modifieds) | 3rd | - | - | 16th |
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| 1/15/2020 | Arizona Speedway - Queen Creek, AZ Wild West Shootout A Modifieds: Wild West Shootout Dirt Super Late Models, B Modifieds, USRA Modifieds, IMCA Modified | Results | | Zach Benson (B Modifieds) | 3rd | - | - | 1st |
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| 1/17/2020 | Arizona Speedway - Queen Creek, AZ Wild West Shootout A Modifieds: Wild West Shootout Dirt Super Late Models, B Modifieds, USRA Modifieds | Results | | Zach Benson (B Modifieds) | 5th | - | - | 5th |
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| 1/18/2020 | Arizona Speedway - Queen Creek, AZ Wild West Shootout A Modifieds: Wild West Shootout Dirt Super Late Models, B Modifieds, USRA Modifieds | Results | | Zach Benson (B Modifieds) | 5th | - | 2nd | 20th |
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| 1/19/2020 | Arizona Speedway - Queen Creek, AZ Wild West Shootout A Modifieds: Wild West Shootout Dirt Super Late Models, B Modifieds, USRA Modifieds | Results | | Zach Benson (B Modifieds) | 8th | - | 1st | 9th |
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| 5/1/2020 | Mississippi Thunder Speedway - Fountain City, WI Weekly Racing Dirt Late Models, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Zach Benson (USRA B-Mods) | 4th | - | - | 8th |
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| 5/15/2020 | Cedar Lake Speedway - New Richmond, WI School Bus Race Night!! 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Midwest Modifieds, 305 Sprints - Non-Winged | Results | | Zach Benson (Midwest Modifieds) | 2nd | - | - | 7th |
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| 5/17/2020 | Casino Speedway - Watertown, SD WISSOTA Dirt Track Series Weekly Racing Dirt Late Models, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Zach Benson (WISSOTA Midwest Mods) | 1st | - | - | 14th (DNF) |
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| 5/23/2020 | Cedar Lake Speedway - New Richmond, WI Pack The Track Night and Cook Memorial FREE GRANDSTAND ENTRY! Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Midwest Modifieds, Winged A-Class, Pony Stock, Super Stocks, USRA Late Models | Results | | Zach Benson (Midwest Modifieds) | 3rd | - | - | 11th |
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| 5/24/2020 | Eagle Valley Speedway - Jim Falls, WI Sunday Night WISSOTA Racing Action Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Hornets, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Zach Benson (WISSOTA Midwest Mods) | 4th | - | - | 3rd |
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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 | | Zach Benson (WISSOTA Midwest Mods) | 1st | - | - | 22nd (DNF) |
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| 5/30/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #5 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Modifieds | Results | | Zach Benson (Midwest Modifieds) | 6th | - | 2nd | 14th |
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| 6/6/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #6 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Zach Benson (Midwest Modifieds) | 5th | - | - | 22nd (DNF) |
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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 | | Zach Benson (WISSOTA Midwest Mods) | 3rd | - | - | 17th (DNF) |
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| 6/13/2020 | Deer Creek Speedway - Spring Valley, MN School Bus Races-Mascot Night-Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Zach Benson (WISSOTA Midwest Mods) | 2nd | - | - | 1st |
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| 6/20/2020 | Ogilvie Raceway - Ogilvie, MN Season Opener USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Zach Benson (WISSOTA Midwest Mods) | 4th | - | - | 6th |
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| 6/26/2020 | Princeton Speedway - Princeton, MN Bill Siercks Memorial Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four | Results | | Zach Benson (A Modifieds) | 4th | - | - | 6th |
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| 6/27/2020 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Zach Benson (WISSOTA Midwest Mods) | 6th (DNF) | - | - | 13th (DNF) |
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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 | | Zach Benson (WISSOTA Midwest Mods) | 4th | - | - | 10th |
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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 | | Zach Benson (WISSOTA Midwest Mods) | 5th | - | - | 9th |
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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 | | Zach Benson (WISSOTA Midwest Mods) | 1st | - | - | 2nd |
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| 7/5/2020 | Eagle Valley Speedway - Jim Falls, WI Sunday Night Fireworks w/ WISSOTA Auto Racing Hornets, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Zach Benson (WISSOTA Midwest Mods) | 1st | - | - | 5th |
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| 7/10/2020 | Gondik Law Speedway - Superior, WI Red Cedar Speedway Night USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Zach Benson (WISSOTA Midwest Mods) | 4th | - | - | 3rd |
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| 7/11/2020 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout with Fireworks Spectacular USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Zach Benson (WISSOTA Midwest Mods) | 3rd | - | - | 3rd |
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| 7/18/2020 | Deer Creek Speedway - Spring Valley, MN Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Zach Benson (WISSOTA Midwest Mods) | 3rd | - | - | 6th |
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| 7/21/2020 | Ogilvie Raceway - Ogilvie, MN School Bus Races with Street Stock Tour Special WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Zach Benson (WISSOTA Midwest Mods) | 1st | - | - | 4th |
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| 7/25/2020 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout with Mod Four Spotlight USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Zach Benson (WISSOTA Midwest Mods) | 1st | - | - | 1st |
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| 7/31/2020 | Mississippi Thunder Speedway - Fountain City, WI K-Town Klash Casey Knutson Memorial USRA B-Mods, USRA Modifieds, USRA Hobby Stocks | Results | | Zach Benson (USRA B-Mods) | 5th | - | 3rd | 17th |
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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 | | Zach Benson (Midwest Modifieds) | 3rd | - | - | 3rd |
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| 8/15/2020 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Zach Benson (WISSOTA Midwest Mods) | 3rd | - | - | 4th |
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| 8/16/2020 | Casino Speedway - Watertown, SD A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Street Stock | Results | | Zach Benson (WISSOTA Midwest Mods) | 1st | - | - | 9th |
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| 8/22/2020 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Zach Benson (WISSOTA Midwest Mods) | 1st | - | - | 6th |
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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 | | Zach Benson (WISSOTA Midwest Mods) | 4th | - | - | 2nd |
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| 9/10/2020 | Mississippi Thunder Speedway - Fountain City, WI 9th Annual Modified Nationals Presented by Dahl Chevy/GMC USRA B-Mods, USRA Modifieds, IMCA Modified | Results | | Zach Benson (USRA B-Mods) | 2nd | - | - | 1st |
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| 9/11/2020 | Mississippi Thunder Speedway - Fountain City, WI 9th Annual Modified Nationals Presented by Dahl Chevy/GMC USRA B-Mods, USRA Modifieds, IMCA Modified | Results | | Zach Benson (USRA B-Mods) | 4th | - | 2nd | 9th |
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| 9/12/2020 | Mississippi Thunder Speedway - Fountain City, WI 9th Annual Modified Nationals Presented by Dahl Chevy/GMC USRA B-Mods, USRA Modifieds, IMCA Modified | Results | | Zach Benson (USRA B-Mods) | 2nd | - | - | 28th (DNF) |
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| 9/17/2020 | Cedar Lake Speedway - New Richmond, WI 15th Annual Legendary 100 Day 1 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods | Results | | Zach Benson (Midwest Modifieds) | - | - | - | 2nd |
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| 9/18/2020 | Cedar Lake Speedway - New Richmond, WI 15th Annual Legendary 100 Day 2 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods | Results | | Zach Benson (Midwest Modifieds) | - | - | - | - |
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| 9/19/2020 | Cedar Lake Speedway - New Richmond, WI 15th Annual Legendary 100 Day 3 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods | Results | | Zach Benson (Midwest Modifieds) | - | - | - | 3rd |
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| 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 | | Zach Benson (WISSOTA Midwest Mods) | 3rd | - | - | - |
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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 | | Zach Benson (WISSOTA Midwest Mods) | - | - | - | 5th |
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