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| 5/6/2023 | Land of Legends - Canandaigua, NY Seneca Meadows & Howell Properties Saturday Spectatular 305 Sprints - Winged, DIRTcar Sportsmans, Hobby Stocks, Street Stocks, DIRTcar Big Block Modifieds, DIRTcar Sportsman Modifieds | Results | | Darryl Ruggles (305 Sprints - Winged) | 2nd | - | - | 2nd |
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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 | | Darryl Ruggles (305 Sprints - Winged) | 1st | - | - | 8th |
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| 5/27/2023 | Land of Legends - Canandaigua, NY Nardozzi Saturday Spectatular 305 Sprints - Winged, DIRTcar Sportsmans, Hobby Stocks, Street Stocks, DIRTcar Big Block Modifieds, DIRTcar Sportsman Modifieds | Results | | Darryl Ruggles (305 Sprints - Winged) | 2nd | - | - | 8th |
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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 | | Darryl Ruggles (305 Sprints - Winged) | 2nd | - | - | 5th |
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| 6/10/2023 | Land of Legends - Canandaigua, NY Ryan Phelps Auto Sales Saturday Night Spectatular 305 Sprints - Winged, DIRTcar Sportsmans, Hobby Stocks, Street Stocks, DIRTcar Big Block Modifieds, DIRTcar Sportsman Modifieds | Results | | Darryl Ruggles (305 Sprints - Winged) | 3rd | - | - | 4th |
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| 6/17/2023 | Land of Legends - Canandaigua, NY Seneca Meadows Saturday Spectatular 305 Sprints - Winged, DIRTcar Sportsmans, Hobby Stocks, Street Stocks, DIRTcar Big Block Modifieds | Results | | Darryl Ruggles (305 Sprints - Winged) | 6th | - | - | 12th |
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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 | | Darryl Ruggles (305 Sprints - Winged) | 3rd | - | - | 15th |
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| 7/8/2023 | Land of Legends - Canandaigua, NY Geneva Club Beverage Saturday Spectatular 305 Sprints - Winged, DIRTcar Sportsmans, Hobby Stocks, Street Stocks, DIRTcar Big Block Modifieds, DIRTcar Sportsman Modifieds | Results | | Darryl Ruggles (305 Sprints - Winged) | 3rd | - | - | 4th |
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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 | | Darryl Ruggles (305 Sprints - Winged) | 8th | - | 1st | 10th |
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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 | | Darryl Ruggles (305 Sprints - Winged) | 4th | - | - | 18th |
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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 | | Darryl Ruggles (305 Sprints - Winged) | 1st | - | - | 3rd |
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| 9/2/2023 | Land of Legends - Canandaigua, NY Prouty's Bar Championship Points Night 305 Sprints - Winged, DIRTcar Sportsmans, Hobby Stocks, Street Stocks, DIRTcar Big Block Modifieds, DIRTcar Sportsman Modifieds | Results | | Darryl Ruggles (305 Sprints - Winged) | 6th | - | - | 8th |
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| 9/22/2023 | Genesee Speedway - Batavia, NY Genesee Speedway $1,000-to-win 305 Sprints - Winged: CRSA Sprint Cars | Results | | Darryl Ruggles (305 Sprints - Winged) | 2nd | - | - | 6th |
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