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| 5/13/2023 | Land of Legends - Canandaigua, NY DisBatch Brewing Co. Challenge Series Race 1 $1,000-to-win 305 Sprints - Winged: CRSA Sprint Cars DIRTcar Sportsmans, Hobby Stocks, Street Stocks, DIRTcar Big Block Modifieds, DIRTcar Sportsman Modifieds | Results | | Tyler Chartrand (305 Sprints - Winged) | 2nd | - | - | 9th |
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| 5/28/2023 | Weedsport Speedway - Weedsport, NY Heroes Remembered 100 305 Sprints - Winged: CRSA Sprint Cars DIRTcar Big Block Modifieds: Super DIRTCar Series | Results | | Tyler Chartrand (305 Sprints - Winged) | 6th | - | 2nd | 23rd (DNF) |
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| 6/3/2023 | Fonda Speedway - Fonda, NY I-90 Pit Stop Challenge Race 2 $1,000-to-win 305 Sprints - Winged: CRSA Sprint Cars Sportsmans, Limited Modified, Pure Stock, Dirt Big Block Modifieds, DIRTcar 4 Cylinders | Results | | Tyler Chartrand (305 Sprints - Winged) | 4th | - | - | 17th |
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| 6/30/2023 | Penn Can Speedway - Susquehanna, PA Penn Can Speedway $1,000-to-win 305 Sprints - Winged: CRSA Sprint Cars | Results | | Tyler Chartrand (305 Sprints - Winged) | 3rd | - | - | 15th |
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| 7/7/2023 | Outlaw Speedway - Dundee, NY Outlaw Speedway Rescheduled $1,000-to-win 305 Sprints - Winged: CRSA Sprint Cars | Results | | Tyler Chartrand (305 Sprints - Winged) | 1st | - | - | 5th |
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| 7/14/2023 | Utica-Rome Speedway - Vernon, NY I-90 Pit Stop Challenge Race 4 $1,000-to-win 305 Sprints - Winged: CRSA Sprint Cars Stock Cars, Sportsmans, Limited Modified, Dirt Big Block Modifieds, DIRTcar 4 Cylinders | Results | | Tyler Chartrand (305 Sprints - Winged) | 3rd | - | - | 11th |
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| 7/22/2023 | Land of Legends - Canandaigua, NY Seneca Meadows & Auction Direct Saturdaty Spectatular 305 Sprints - Winged: CRSA Sprint Cars DIRTcar Sportsmans, Hobby Stocks, Street Stocks, DIRTcar Big Block Modifieds, DIRTcar Sportsman Modifieds | Results | | Tyler Chartrand (305 Sprints - Winged) | 2nd | - | - | 5th |
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| 7/23/2023 | Thunder Mountain Speedway - Center Lisle, NY Thunder Mountain (NY) $1,000-to-win 305 Sprints - Winged: CRSA Sprint Cars | Results | | Tyler Chartrand (305 Sprints - Winged) | 1st | - | - | 5th |
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| 8/5/2023 | Land of Legends - Canandaigua, NY DisBatch Brewing Co. Challenge Series Race 3 $1,000-to-win 305 Sprints - Winged: CRSA Sprint Cars DIRTcar Sportsmans, Hobby Stocks, Street Stocks, DIRTcar Big Block Modifieds | Results | | Tyler Chartrand (305 Sprints - Winged) | 4th | - | - | 12th |
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| 8/19/2023 | Woodhull Raceway - Woodhull, NY Woodhull Raceway $1,000-to-win 305 Sprints - Winged: CRSA Sprint Cars Hobby Stocks, Stock Cars, Street Stocks, Dirt 6-cyl Stock Cars, Dirt Big Block Modifieds, RUSH Late Models, RUSH Sportsman Modified, Dirt Mini Stocks | Results | | Tyler Chartrand (305 Sprints - Winged) | 7th | - | 2nd | 21st (DNF) |
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| 8/25/2023 | Albany-Saratoga Speedway - Malta, NY Albany-Saratoga Speedway $1,000-to-win 305 Sprints - Winged: CRSA Sprint Cars | Results | | Tyler Chartrand (305 Sprints - Winged) | 6th | - | - | 20th |
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| 9/15/2023 | Fonda Speedway - Fonda, NY I-90 Pit Stop Challenge Race 6 $1,000-to-win 305 Sprints - Winged: CRSA Sprint Cars Dirt Big Block Modifieds: Short Track Super Series Street Stocks, Pure Stock, DIRTcar 4 Cylinders | Results | | Tyler Chartrand (305 Sprints - Winged) | 4th | - | - | 23rd |
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