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| 5/9/2020 | North Central Speedway - Brainerd, MN Season opener Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car | Canceled |
| 5/15/2020 | Mississippi Thunder Speedway - Fountain City, WI Weekly Racing Dirt Late Models, Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Terry Matthewman (Hornets) | 15th (DNF) | - | - | 29th (DNF) |
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| 5/16/2020 | North Central Speedway - Brainerd, MN Brainerd Invitional Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Canceled |
| 6/5/2020 | North Central Speedway - Brainerd, MN Opener B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Terry Matthewman (Sport Compact) | 4th | - | - | 24th |
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| 6/6/2020 | North Central Speedway - Brainerd, MN Weekly Races Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car | Rain Out |
| 6/7/2020 | North Central Speedway - Brainerd, MN Night 3 Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car | Results | | Terry Matthewman (Sport Compact) | 6th | - | - | 22nd (DNF) |
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| 6/12/2020 | Princeton Speedway - Princeton, MN Season OPENER 360 Sprints - Winged: Midwest Power Series Limited Sprints - Winged: Upper Midwest Sprint Car Series Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Terry Matthewman (Sport Compact) | 8th | - | - | 14th |
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| 6/13/2020 | North Central Speedway - Brainerd, MN Weekly Racing plus IMCA Stock Cars Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Terry Matthewman (Sport Compact) | 5th | - | - | DNS |
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| 6/19/2020 | Princeton Speedway - Princeton, MN Weekly Racing Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Terry Matthewman (Sport Compact) | 8th | - | - | 16th |
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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 | | Terry Matthewman (WISSOTA Hornet) | 8th (DNF) | - | - | 24th (DNF) |
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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 | | Terry Matthewman (Sport Compact) | 6th (DNF) | - | - | 18th (DNF) |
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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 | | Terry Matthewman (WISSOTA Hornet) | 5th | - | - | 12th |
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| 7/3/2020 | Princeton Speedway - Princeton, MN Weekly races Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Terry Matthewman (Sport Compact) | 8th | - | - | 6th |
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| 7/4/2020 | North Central Speedway - Brainerd, MN Races Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Terry Matthewman (Sport Compact) | 3rd | - | - | 1st |
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| 7/10/2020 | Princeton Speedway - Princeton, MN Weekly Racing 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Terry Matthewman (Sport Compact) | 6th | - | - | DNS |
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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 | | Terry Matthewman (WISSOTA Hornet) | 6th | - | - | 14th |
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| 7/17/2020 | Princeton Speedway - Princeton, MN FastLane Super Stock Series WISSOTA Super Stock: Fast Lane Motorsports Northland Super Stock Series Hobby Stocks, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four | Results | | Terry Matthewman (Sport Compact) | 5th | - | - | 15th |
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| 7/24/2020 | Princeton Speedway - Princeton, MN Weekly Racing Vintage Modifieds: Northern Vintage Stockcar Racers Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, 360 Sprints - Non-Winged, Vintage Full Body Stock Cars, Sport Compact, IMCA Stock Car, WISSOTA Mod Four | Results | | Terry Matthewman (Sport Compact) | DNS | - | - | 16th |
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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 | | Terry Matthewman (WISSOTA Hornet) | 8th (DNF) | - | - | 21st (DNF) |
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| 7/31/2020 | Princeton Speedway - Princeton, MN Hobby Stock Tour Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Terry Matthewman (Sport Compact) | 8th | - | - | 11th |
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| 8/1/2020 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout Fast Lane Super Stock Series WISSOTA Super Stock: Fast Lane Motorsports Northland Super Stock Series WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Terry Matthewman (WISSOTA Hornet) | 7th | - | - | 22nd (DNF) |
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| 9/4/2020 | Princeton Speedway - Princeton, MN Season Championship Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Terry Matthewman (Sport Compact) | 9th | - | - | 21st |
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| 9/5/2020 | North Central Speedway - Brainerd, MN Mighty Axe Day 1 Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Sport Compact, All Star Slingshots, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Terry Matthewman (Sport Compact) | 3rd | - | - | 28th (DNF) |
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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 | | Terry Matthewman (WISSOTA Hornet) | - | - | - | - |
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