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| 4/17/2021 | Cedar Lake Speedway - New Richmond, WI Legendary Open 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 Late Models | Results | | Josh Winsky (Pony Stock) | - | - | - | 18th (DNF) |
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| 4/23/2021 | Mississippi Thunder Speedway - Fountain City, WI 13th Annual Season Opener presented by Kelly Iverson Trucking Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Josh Winsky (Hornets) | 5th | - | - | 21st |
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| 4/30/2021 | 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 | - | - | 10th (DNF) |
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| 5/7/2021 | Chateau Speedway - Lansing, MN Season Opener Regular Friday Night 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) | 8th | - | - | 10th |
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| 5/14/2021 | Chateau Speedway - Lansing, MN Regular Friday Night 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) | 1st | - | - | 15th (DNF) |
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| 5/28/2021 | Princeton Speedway - Princeton, MN Late Model Show WISSOTA Late Model: Wissota Late Model Challenge Series Hobby Stocks, Sport Compact, IMCA Stock Car | Results | | Josh Winsky (Sport Compact) | DNS | - | - | DNS |
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| 5/29/2021 | Cedar Lake Speedway - New Richmond, WI Pack The Track Night / Cook Memorial Winged A-Class, Pony Stock, Super Stocks, USRA Late Models | Results | | Josh Winsky (Pony Stock) | 1st | - | - | 14th |
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| 6/4/2021 | Chateau Speedway - Lansing, MN Regular Friday Night 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 | - | - | 2nd |
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| 6/11/2021 | Chateau Speedway - Lansing, MN Regular Friday Night 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) | 1st | - | - | 13th (DNF) |
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| 6/18/2021 | Chateau Speedway - Lansing, MN UMSS Non Wing Traditional Sprint Special #1 360 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 | - | - | 1st |
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| 7/2/2021 | Chateau Speedway - Lansing, MN Regular Friday Night Racing USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Hornet) | 7th (DNF) | - | - | 4th |
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| 7/9/2021 | Red Cedar Speedway - Menomonie, WI Military Night: All Military Personnel Get in FREE with Military I.D. Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Josh Winsky (Hornets) | 5th | - | - | DNS |
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| 7/16/2021 | Chateau Speedway - Lansing, MN UMSS Non Wing Traditional Sprint Special #2 360 Sprints - Non-Winged, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Hornet) | 2nd | - | - | 12th (DNF) |
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| 7/23/2021 | Chateau Speedway - Lansing, MN Hall of Fame Induction Night USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Hornet) | 2nd | - | - | 6th (DNF) |
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| 7/30/2021 | Mississippi Thunder Speedway - Fountain City, WI K-Town Klash USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Josh Winsky (USRA B-Mods) | 9th | - | 15th | - |
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| 7/31/2021 | Deer Creek Speedway - Spring Valley, MN Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Rain Out |
| 8/3/2021 | Deer Creek Speedway - Spring Valley, MN 2021 IMCA Harris Clash IMCA Modified, IMCA Northern SportMod | Results | | Josh Winsky (IMCA Northern SportMod) | 9th (DNF) | - | 11th | - |
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| 8/6/2021 | Chateau Speedway - Lansing, MN Regular Friday Night Racing. Race of Champions. Sprints 360 Sprints - Non-Winged, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Midwest Mods) | 9th (DNF) | - | - | 14th (DNF) |
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| 8/13/2021 | Chateau Speedway - Lansing, MN Fireworks and Regular racing USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Midwest Mods) | 4th | - | - | 19th (DNF) |
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| 8/14/2021 | Deer Creek Speedway - Spring Valley, MN Veterans Night- Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Josh Winsky (WISSOTA Midwest Mods) | 7th | - | - | 18th |
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| 8/20/2021 | Chateau Speedway - Lansing, MN Kids Night-Car Rides and Bicycle give aways USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Midwest Mods) | 7th | - | - | - |
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| 8/21/2021 | Deer Creek Speedway - Spring Valley, MN Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Josh Winsky (WISSOTA Midwest Mods) | 7th | - | - | 18th (DNF) |
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| 8/29/2021 | Granite City Motor Park - Sauk Rapids, MN Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series A Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Midwest Mods) | 7th (DNF) | - | - | 10th |
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| 9/4/2021 | Deer Creek Speedway - Spring Valley, MN 16th Annual USMTS Labor Day Duel A Modifieds: USMTS - United States Modified Touring Series USRA B-Mods, USRA Late Models, USRA Stock Cars | Results | | Josh Winsky (USRA B-Mods) | 8th | - | 13th (DNF) | - |
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| 9/5/2021 | Fayette County Speedway - West Union, IA USMTS A Modifieds: USMTS - United States Modified Touring Series USRA B-Mods, USRA Modifieds, USRA Hobby Stocks, USRA Stock Cars | Results | | Josh Winsky (USRA B-Mods) | 6th | - | 11th | - |
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| 9/10/2021 | Chateau Speedway - Lansing, MN Spirit of 83 Rescheduled Event Night USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Midwest Mods) | 7th | - | - | 18th (DNF) |
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| 9/11/2021 | Chateau Speedway - Lansing, MN National Points Special USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Josh Winsky (WISSOTA Midwest Mods) | 6th | - | - | 17th (DNF) |
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| 9/16/2021 | Cedar Lake Speedway - New Richmond, WI 16th Annual Legendary 100 Night 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 Late Models, WISSOTA Midwest Mods | Results | | Josh Winsky (Midwest Modifieds) | - | - | - | 18th |
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| 9/17/2021 | Cedar Lake Speedway - New Richmond, WI 16th Annual Legendary 100 Night 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 Late Models, WISSOTA Midwest Mods | Results | | Josh Winsky (Midwest Modifieds) | - | - | - | - |
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| 9/18/2021 | Cedar Lake Speedway - New Richmond, WI 16th Annual Legendary 100 Night 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 Late Models, WISSOTA Midwest Mods | Results | | Josh Winsky (Midwest Modifieds) | - | - | 15th (DNF) | - |
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| 9/23/2021 | Deer Creek Speedway - Spring Valley, MN 23rd Annual Featherlite Fall Jamboree USRA B-Mods, USRA Modifieds | Results | | Josh Winsky (USRA B-Mods) | 10th | - | 11th | - |
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| 9/24/2021 | Deer Creek Speedway - Spring Valley, MN 23rd Annual Featherlite Fall Jamboree A Modifieds: USMTS - United States Modified Touring Series USRA B-Mods | Results | | Josh Winsky (USRA B-Mods) | 10th | - | 8th | - |
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| 9/25/2021 | Deer Creek Speedway - Spring Valley, MN 23rd Annual Featherlite Fall Jamboree A Modifieds: USMTS - United States Modified Touring Series USRA B-Mods | Results | | Josh Winsky (USRA B-Mods) | 5th | - | 9th | - |
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| 10/1/2021 | Mississippi Thunder Speedway - Fountain City, WI The Great Pumpkin Race Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks, USRA Stock Cars | Results | | Josh Winsky (USRA B-Mods) | 8th | - | 11th | - |
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| 10/2/2021 | Mississippi Thunder Speedway - Fountain City, WI The Great Pumpkin Race Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks, USRA Stock Cars | Results | | Josh Winsky (USRA B-Mods) | 7th | - | 8th | - |
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| 10/8/2021 | Ogilvie Raceway - Ogilvie, MN Fall Classic presented by FYE Motorsports A Modifieds, USRA Late Models, 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 Midwest Mods) | DNS | - | - | - |
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| 10/9/2021 | Ogilvie Raceway - Ogilvie, MN Fall Classic presented by FYE Motorsports A Modifieds, USRA Late Models, 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 Midwest Mods) | - | - | DNS | - |
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| 10/16/2021 | Mason City Motor Speedway - Mason City, IA Five Star Classic 600cc Modifieds, USRA B-Mods, USRA Modifieds, USRA Hobby Stocks, USRA Stock Cars, USRA Tuners | Results | | Josh Winsky (USRA Tuners) | 3rd | - | - | 7th |
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| 10/17/2021 | Mason City Motor Speedway - Mason City, IA Five Star Classic 600cc Modifieds, USRA B-Mods, USRA Modifieds, USRA Hobby Stocks, USRA Stock Cars, USRA Tuners | Results | | Josh Winsky (USRA Tuners) | 6th | - | - | 9th |
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