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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 | | Randy Jacoboski (Hornets) | 10th | - | - | 12th |
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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 |
| 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 | | Randy Jacoboski (WISSOTA Hornet) | 4th | - | - | 10th |
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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 | | Randy Jacoboski (Pony Stock) | 6th | - | - | 17th |
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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 | | Randy Jacoboski (Sport Compact) | 4th | - | - | 11th |
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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 | | Randy Jacoboski (WISSOTA Hornet) | 4th | - | - | 12th |
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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 | | Randy Jacoboski (Sport Compact) | 3rd | - | - | 14th |
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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 | | Randy Jacoboski (Sport Compact) | 2nd | - | - | 2nd |
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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 | | Randy Jacoboski (WISSOTA Hornet) | 1st | - | - | 5th |
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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 | | Randy Jacoboski (Sport Compact) | 1st | - | - | 19th |
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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 | | Randy Jacoboski (WISSOTA Hornet) | 3rd | - | - | 5th |
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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 | | Randy Jacoboski (Sport Compact) | 3rd | - | - | 5th |
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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 | | Randy Jacoboski (WISSOTA Hornet) | 7th (DNF) | - | - | 7th |
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| 8/8/2020 | North Central Speedway - Brainerd, MN Weekly Races Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Randy Jacoboski (Sport Compact) | 4th | - | - | 11th |
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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 | | Randy Jacoboski (WISSOTA Hornet) | 4th | - | - | 7th |
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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 | | Randy Jacoboski (WISSOTA Hornet) | 1st | - | - | 18th (DNF) |
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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 | | Randy Jacoboski (WISSOTA Hornet) | 3rd | - | - | 5th |
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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 | | Randy Jacoboski (WISSOTA Hornet) | 1st | - | - | 5th |
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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 | | Randy Jacoboski (WISSOTA Hornet) | 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 | | Randy Jacoboski (WISSOTA Hornet) | - | - | - | 21st (DNF) |
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