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| 4/15/2023 | Beaver Dam Raceway - Beaver Dam, WI Jim Wipperfurth Memorial with IRA 410 Sprints 410 Sprints - Winged: IRA Interstate Racing Association Pro Legends: Midwest Legends Dirt Series Street Stocks | Results | | Matt Gritt (Pro Legends) | 6th | - | - | 10th |
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| 5/12/2023 | Outagamie Speedway - Seymour, WI The Wisconsin Dirt Legends make a visit to Outagamie Speedway Pro Legends: Midwest Legends Dirt Series Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Matt Gritt (Pro Legends) | 4th | - | - | - |
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| 5/21/2023 | Angell Park Speedway - Sun Prairie, WI "The Dalhke Memorial" Season Opener at Angell Park 410 Sprints - Winged: IRA Interstate Racing Association Pro Legends: Midwest Legends Dirt Series Badger Midgets: Badger Midget Auto Racing Association | Results | | Matt Gritt (Pro Legends) | 6th | - | - | 9th |
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| 5/28/2023 | 141 Speedway - Maribel, WI Sunday Funday with the Bumper to Bumper IRA Sprints, Lightning Sprints and Sport Compacts 410 Sprints - Winged: IRA Interstate Racing Association Pro Legends: Midwest Legends Dirt Series Lightning Sprints: IRA Lightning Sprints Sport Compact | Results | | Matt Gritt (Pro Legends) | 4th | - | - | 7th |
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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 | | Matt Gritt (Pro Legends) | 3rd | - | - | 7th |
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| 6/16/2023 | Beaver Dam Raceway - Beaver Dam, WI Jim JB Boyd Memorial with World of Outlaws Sprints Night 1 410 Sprints - Winged: World of Outlaws Winged Outlaw: Minnesota Micro Sprints Pro Legends: Midwest Legends Dirt Series | Results | | Matt Gritt (Pro Legends) | 5th | - | - | 12th |
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| 6/17/2023 | Beaver Dam Raceway - Beaver Dam, WI Jim JB Boyd Memorial with World of Outlaws Sprints Night 2 410 Sprints - Winged: World of Outlaws Winged Outlaw: Minnesota Micro Sprints Pro Legends: Midwest Legends Dirt Series | Results | | Matt Gritt (Pro Legends) | 6th | - | - | 21st (DNF) |
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| 6/24/2023 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI Weekly Racing with Wisconsin Dirt Legends Pro Legends: Midwest Legends Dirt Series 360 Sprints - Winged, Stock Cars, Limited Modified | Results | | Matt Gritt (Pro Legends) | 5th | - | - | 6th |
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| 7/8/2023 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI Weekly Racing with Wisconsin Dirt Legends Pro Legends: Midwest Legends Dirt Series 360 Sprints - Winged, Stock Cars, Limited Modified | Results | | Matt Gritt (Pro Legends) | 2nd | - | - | 5th |
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| 7/28/2023 | 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 | | Matt Gritt (Pro Legends) | 4th | - | - | 8th |
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| 8/1/2023 | Beaver Dam Raceway - Beaver Dam, WI 5 Division Night + High School Racing Association - Back to School Night Hobby Stocks, Street Stocks, Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Matt Gritt (Pro Legends) | 2nd | - | - | 7th |
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| 8/8/2023 | Beaver Dam Raceway - Beaver Dam, WI 5 Division Night - IMCA Stock Car All Star Qualifier $1000 to Win Street Stocks, Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Matt Gritt (Pro Legends) | 5th | - | - | 5th |
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| 8/19/2023 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI Weekly Racing with Wisconsin Dirt Legends Pro Legends: Midwest Legends Dirt Series 360 Sprints - Winged, Stock Cars, Limited Modified | Results | | Matt Gritt (Pro Legends) | 4th | - | - | 8th |
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| 8/29/2023 | Beaver Dam Raceway - Beaver Dam, WI 5 Division Night - 2 for the price of 1 Soda Night Street Stocks, Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Matt Gritt (Pro Legends) | 4th | - | - | - |
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| 9/16/2023 | 141 Speedway - Maribel, WI Bumper to Bumper IRA Sprints, Lightning Sprints, Legends and Street Stocks 410 Sprints - Winged: IRA Interstate Racing Association Pro Legends: Midwest Legends Dirt Series Lightning Sprints: IRA Lightning Sprints Hobby Stocks | Rain Out |
| 10/7/2023 | Beaver Dam Raceway - Beaver Dam, WI Pink Hat Fall Classic Stock Cars, Street Stocks, Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Matt Gritt (Pro Legends) | 3rd | - | - | 11th |
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