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| 4/14/2023 | Gravity Park Speedway - Chilton, WI Races on the Speedway DIRTcar Sport Compact, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Super Stocks | Results | | Jack Wiroll (Street Stocks) | 6th | - | - | 15th (DNF) |
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| 4/21/2023 | Gravity Park Speedway - Chilton, WI Races on the Speedway DIRTcar Sport Compact, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Super Stocks | Results | | Jack Wiroll (Street Stocks) | 8th (DNF) | - | - | 12th (DNF) |
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| 4/28/2023 | Gravity Park Speedway - Chilton, WI Races on the Speedway DIRTcar Sport Compact, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Super Stocks | Results | | Jack Wiroll (Street Stocks) | 5th | - | - | 19th (DNF) |
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| 5/5/2023 | Gravity Park Speedway - Chilton, WI Races on the Speedway DIRTcar Sport Compact, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Super Stocks | Results | | Jack Wiroll (Street Stocks) | 1st | - | - | 2nd |
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| 5/19/2023 | Gravity Park Speedway - Chilton, WI Races on the Speedway DIRTcar Sport Compact, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Vintage Modifieds, Super Stocks | Results | | Jack Wiroll (Street Stocks) | 5th | - | - | 11th (DNF) |
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| 5/26/2023 | Gravity Park Speedway - Chilton, WI Races on the Speedway DIRTcar Sport Compact, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Super Stocks | Results | | Jack Wiroll (Street Stocks) | 1st | - | - | 2nd |
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| 6/2/2023 | Gravity Park Speedway - Chilton, WI Races on the Speedway DIRTcar Sport Compact, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Super Stocks | Results | | Jack Wiroll (Street Stocks) | 3rd | - | - | 14th |
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| 6/9/2023 | Gravity Park Speedway - Chilton, WI Races on the Speedway Pro Legends: Midwest Legends Dirt Series DIRTcar Sport Compact, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Super Stocks | Results | | Jack Wiroll (Street Stocks) | 1st | - | - | 4th |
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| 6/16/2023 | Gravity Park Speedway - Chilton, WI Gravity Park USA Badger Midgets: Badger Midget Auto Racing Association DIRTcar Sport Compact, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Vintage Modifieds, Super Stocks | Results | | Jack Wiroll (Street Stocks) | 7th (DNF) | - | - | 8th |
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| 6/23/2023 | Gravity Park Speedway - Chilton, WI King of the Bullring DIRTcar Sport Compact, B Modifieds, Street Stocks, Dirt Late Models, Super Stocks | Results | | Jack Wiroll (Street Stocks) | 4th | - | - | 14th |
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| 7/15/2023 | 141 Speedway - Maribel, WI Pepsi Presents Fan Appreciation Night - $1,000 to Win Unified Street Stocks Stock Cars, Sportsmans, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Jack Wiroll (Sportsmans) | 8th | - | 8th | - |
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| 7/21/2023 | Gravity Park Speedway - Chilton, WI Races on the Speedway DIRTcar Sport Compact, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Vintage Modifieds, Super Stocks | Results | | Jack Wiroll (Street Stocks) | 4th | - | - | DNS |
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| 7/29/2023 | 141 Speedway - Maribel, WI Robinson Presents Driver Appreciation w/ the Powder Puff | Uni. Street Stocks Blue Race $1000 to Win Stock Cars, Sportsmans, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Jack Wiroll (Sportsmans) | 5th | - | 4th | 21st (DNF) |
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| 8/4/2023 | Gravity Park Speedway - Chilton, WI Races on the Speedway DIRTcar Sport Compact, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Super Stocks | Results | | Jack Wiroll (Street Stocks) | 4th | - | - | 8th |
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| 8/11/2023 | Gravity Park Speedway - Chilton, WI Races on the Speedway DIRTcar Sport Compact, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Super Stocks | Results | | Jack Wiroll (Street Stocks) | 1st | - | - | DNS |
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| 8/25/2023 | Gravity Park Speedway - Chilton, WI Races on the Speedway DIRTcar Sport Compact, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Super Stocks | Results | | Jack Wiroll (Street Stocks) | 3rd | - | - | DNS |
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| 9/1/2023 | Eagle River Speedway - Eagle River, WI Season Finale! Out with a Bang - Two Day Special! Stock Cars, B Modifieds, Street Stocks, Vintage Full Body Stock Cars, Junior Sprints, Pure Stock | Results | | Jack Wiroll (Street Stocks) | 6th | - | - | - |
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| 9/2/2023 | Eagle River Speedway - Eagle River, WI Season Finale! Out with a Bang - Two Day Special! Winged Sprints, Stock Cars, Winged A-Class, B Modifieds, Street Stocks, Dirt Late Models, Junior Sprints, Super Stocks | Results | | Jack Wiroll (Street Stocks) | - | - | - | 4th |
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| 9/15/2023 | Gravity Park Speedway - Chilton, WI 2023 Chilton Fall Classic DIRTcar Sport Compact, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Trophy Truck, Super Stocks | Results | | Jack Wiroll (Street Stocks) | DNS | - | - | - |
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| 9/16/2023 | Gravity Park Speedway - Chilton, WI 2023 Chilton Fall Classic DIRTcar Sport Compact, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Super Stocks | Results | | Jack Wiroll (Street Stocks) | - | - | - | - |
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| 9/23/2023 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI 6th Annual Wildman Watson Classic Dirt Late Models: Dirt Kings Late Model Tour Non Wing Crate Sprints: Wisconsin wingLESS Sprints A Modifieds, Street Stocks, IMCA Modified | Results | | Jack Wiroll (Street Stocks) | 8th (DNF) | - | - | - |
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