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| 4/16/2021 | Cedar Lake Speedway - New Richmond, WI Legendary Opener 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 Late Models | Results | | Jason Schill (Super Stocks) | - | - | - | 5th |
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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 | | Jason Schill (Super Stocks) | - | - | - | 14th |
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| 5/1/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #4 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Jason Schill (Super Stocks) | 1st | - | - | 3rd |
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| 5/8/2021 | Rice Lake Speedway - Rice Lake, WI Five Class Program WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Schill (WISSOTA Super Stock) | 6th | - | - | 16th (DNF) |
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| 5/22/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #5 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Jason Schill (Super Stocks) | 5th | - | - | 5th |
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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 | | Jason Schill (Super Stocks) | 1st | - | - | 3rd |
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| 5/30/2021 | Ogilvie Raceway - Ogilvie, MN MN Modified Nationals presented by FYE Motorsports WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jason Schill (WISSOTA Super Stock) | 6th | - | - | 16th |
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| 6/12/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #7 / Kids Night Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Super Stocks | Results | | Jason Schill (Super Stocks) | 5th | - | - | 7th |
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| 6/17/2021 | Cedar Lake Speedway - New Richmond, WI 22nd Annual Masters A Modifieds, Dirt Late Models, USRA Modifieds, USRA Late Models | Results | | Jason Schill (Dirt Late Models) | 2nd | - | - | 21st |
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| 6/18/2021 | Cedar Lake Speedway - New Richmond, WI 22nd Annual Masters A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA Late Models, WISSOTA Modifieds | Results | | Jason Schill (Dirt Late Models) | 8th | - | 17th | - |
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| 6/19/2021 | Cedar Lake Speedway - New Richmond, WI 22nd Annual Masters Limited Sprints - Winged: Upper Midwest Sprint Car Series A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA Late Models, WISSOTA Modifieds | Results | | Jason Schill (Dirt Late Models) | 4th | - | - | 20th |
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| 6/26/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Jason Schill (WISSOTA Super Stock) | 7th | - | - | 14th (DNF) |
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| 7/2/2021 | Red Cedar Speedway - Menomonie, WI Bob Zebro 4th of July Shootout Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Schill (WISSOTA Super Stock) | 1st | - | - | 5th |
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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 | | Jason Schill (WISSOTA Super Stock) | 4th | - | - | 5th |
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| 7/10/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #9 / Modified $5,000 To Win A Modifieds, Midwest Modifieds, Dirt Late Models, Super Stocks, USRA Late Models | Results | | Jason Schill (Super Stocks) | 5th | - | - | 10th |
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| 7/17/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #10 / Pro Stock $5,000 To Win 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series 305 Sprints - Non-Winged, 600cc Modifieds, Super Stocks, USRA Late Models | Results | | Jason Schill (Super Stocks) | 2nd | - | - | 22nd |
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| 8/20/2021 | Red Cedar Speedway - Menomonie, WI Final Track Points Night (Mahder 55 Rain Date) Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Schill (WISSOTA Super Stock) | 5th | - | - | 9th |
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| 8/21/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #14 / Season Championship 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Jason Schill (Super Stocks) | 2nd | - | - | 10th |
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| 9/4/2021 | Rice Lake Speedway - Rice Lake, WI Holiday Season Finale, $1000 to win Pure Stocks (Increased pay all classes) WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Schill (WISSOTA Super Stock) | 3rd | - | - | 8th |
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| 9/10/2021 | Eagle Valley Speedway - Jim Falls, WI 2nd Annual - Dalbeck Logging - Union Trailer & Power Equipment Jim Town Showdown A Modifieds, B Modifieds, Street Stocks, Super Stocks, Pure Stock, USRA Late Models, WISSOTA Modifieds | Results | | Jason Schill (Super Stocks) | 4th | - | - | 14th |
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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 | | Jason Schill (Super Stocks) | - | - | - | - |
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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 | | Jason Schill (Super Stocks) | - | - | - | 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 | | Jason Schill (WISSOTA Late Model) | 4th | - | - | - | | Jason Schill (WISSOTA Super Stock) | 6th | - | - | - |
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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 | | Jason Schill (WISSOTA Late Model) | - | - | - | 16th | | Jason Schill (WISSOTA Super Stock) | - | - | 13th (DNF) | - |
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