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| 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 | | Josh Winsky (Hornets) | 11th | - | - | 18th |
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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 | | Josh Winsky (Pony Stock) | 4th | - | - | 18th |
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| 5/29/2020 | Mississippi Thunder Speedway - Fountain City, WI Military Night Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks, WISSOTA Super Stock | Results | | Josh Winsky (Hornets) | 6th | - | - | 13th |
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| 6/5/2020 | Mississippi Thunder Speedway - Fountain City, WI Leighton Broadcasting/Bud Night Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Josh Winsky (Hornets) | 4th | - | - | 15th (DNF) |
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| 6/6/2020 | Winneshiek Raceway - Decorah, IA Points Race Sponsored by Bodenstiener Implement (Decorah) USRA B-Mods, USRA Hobby Stocks, USRA Stock Cars, USRA Tuners, Mod Lites | Results | | Josh Winsky (USRA Tuners) | 7th | - | - | 5th |
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| 6/12/2020 | Mississippi Thunder Speedway - Fountain City, WI Beahman Law Redneck 100 Challenge Hornets, USRA B-Mods, USRA Hobby Stocks | Results | | Josh Winsky (Hornets) | - | - | - | 10th (DNF) |
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| 6/26/2020 | Mississippi Thunder Speedway - Fountain City, WI Weekly Racing Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Josh Winsky (Hornets) | 7th | - | - | 12th |
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| 7/3/2020 | Chateau Speedway - Lansing, MN Season Opener USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Hornet) | 1st | - | - | 14th |
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| 7/10/2020 | Chateau Speedway - Lansing, MN Weekly Racing USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Hornet) | 6th (DNF) | - | - | 17th (DNF) |
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| 7/24/2020 | Chateau Speedway - Lansing, MN Weekly Racing. Soak The Flagman - Water Balloons USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Hornet) | 3rd | - | - | 7th |
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| 7/25/2020 | Winneshiek Raceway - Decorah, IA POINTS RACE sponsored by The Place in Protivin USRA B-Mods, USRA Hobby Stocks, USRA Stock Cars, USRA Tuners, Mod Lites | Results | | Josh Winsky (USRA Tuners) | DNS | - | - | 8th (DNF) |
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| 7/31/2020 | Chateau Speedway - Lansing, MN Weekly Racing USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Hornet) | 6th (DNF) | - | - | 14th (DNF) |
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| 8/7/2020 | Chateau Speedway - Lansing, MN Traditional Non Wing Sprints - Fireworks 360 Sprints - Non-Winged, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Hornet) | 1st | - | - | 5th |
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| 8/8/2020 | Winneshiek Raceway - Decorah, IA Points Race Sponsored by LetterWerks Sign City Decorah USRA B-Mods, USRA Hobby Stocks, USRA Stock Cars, USRA Tuners, Mod Lites | Results | | Josh Winsky (USRA Tuners) | 7th | - | - | 7th |
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| 8/14/2020 | Chateau Speedway - Lansing, MN Weekly Racing. 7 Classes USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Hornet) | 1st | - | - | 7th |
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| 8/21/2020 | Fayette County Speedway - West Union, IA Weekly Races - Season Championships 600cc Modifieds, USRA B-Mods, USRA Hobby Stocks, USRA Stock Cars, USRA Tuners, Dirt Mini Late Models | Results | | Josh Winsky (USRA Tuners) | 7th (DNF) | - | - | 10th |
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| 8/22/2020 | Winneshiek Raceway - Decorah, IA POINTS RACE USRA B-Mods, USRA Hobby Stocks, USRA Stock Cars, USRA Tuners, Mod Lites | Results | | Josh Winsky (USRA Tuners) | 3rd | - | - | 7th |
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| 8/28/2020 | Chateau Speedway - Lansing, MN Weekly Racing. USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Hornet) | 3rd | - | - | 18th (DNF) |
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| 9/4/2020 | Chateau Speedway - Lansing, MN Weekly Racing Last points night all classes A Modifieds: USMTS - United States Modified Touring Series USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Hornet) | 3rd | - | - | 4th |
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| 9/12/2020 | Tri County Speedway - Wishek, ND Sauerkraut 500 Hobby Stocks, A Modifieds, Young Lions Legends, Sport Compact, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Josh Winsky (Sport Compact) | 2nd | - | - | 8th |
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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 | | Josh Winsky (Pony Stock) | - | - | - | 21st (DNF) |
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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 | | Josh Winsky (Pony Stock) | - | - | - | 10th |
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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 | | Josh Winsky (Pony Stock) | - | - | - | 20th (DNF) |
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| 10/2/2020 | Chateau Speedway - Lansing, MN 3rd Annual Extravaganza Night 1 Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Hornet) | 3rd | - | - | 25th (DNF) |
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| 10/3/2020 | Chateau Speedway - Lansing, MN 3rd Annual Extravaganza Night 2 Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Hornet) | 4th | - | - | 1st |
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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 | | Josh Winsky (WISSOTA Hornet) | 7th | - | - | - |
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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 | | Josh Winsky (WISSOTA Hornet) | - | - | 6th | 15th |
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