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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 | | Dan Bennett (305 Sprints - Winged) | DNS | - | - | DNS |
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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 | | Dan Bennett (305 Sprints - Winged) | 6th | - | - | 14th |
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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 | | Dan Bennett (305 Sprints - Winged) | 4th | - | - | 12th |
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| 7/14/2023 | Freedom Speedway - Delevan, NY 360 Sprints - Winged: Empire Super Sprints | Results | | Dan Bennett (360 Sprints - Winged) | 6th | 5th | - | 18th |
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| 7/28/2023 | Outlaw Speedway - Dundee, NY Outlaw Summer Nationals 360 Sprints - Winged: Empire Super Sprints Dirt Super Late Models: ULMS--United Late Model Series | Results | | Dan Bennett (360 Sprints - Winged) | 7th | - | - | 20th |
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| 8/4/2023 | Utica-Rome Speedway - Vernon, NY Makeup for 8/4/23 360 Sprints - Winged: Empire Super Sprints Stock Cars, Sportsmans, Limited Modified, Dirt Big Block Modifieds, DIRTcar 4 Cylinders | Postponed |
| 8/18/2023 | Ransomville Speedway - Ransomville, NY 716 Night 360 Sprints - Winged: Southern Ontario Sprints DIRTcar Sportsmans, Factory Stocks, A Modifieds, Street Stocks | Results | | Dan Bennett (360 Sprints - Winged) | 4th | - | - | 9th |
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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 | | Dan Bennett (305 Sprints - Winged) | 4th | - | - | 8th |
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| 8/26/2023 | 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 | | Dan Bennett (305 Sprints - Winged) | 7th | - | - | 4th |
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| 9/1/2023 | Brewerton Speedway - Brewerton, NY STOP-DWI New York presents ESS Sprints plus Championship Night 360 Sprints - Winged: Empire Super Sprints DIRTcar Big Block Modifieds, DIRTcar Sportsman Modifieds, DIRTcar Mod Lites | Results | | Dan Bennett (360 Sprints - Winged) | 10th | - | 8th | - |
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| 9/2/2023 | Fulton Speedway - Fulton, NY STOP-DWI New York ESS Sprints/Mods/Dbl Sportsman Features/Dbl Novice Features/Hobby Stocks 360 Sprints - Winged: Empire Super Sprints Hobby Stocks, Limited Sport Mod, DIRTcar 358 Modifieds, DIRTcar Sportsman Modifieds | Results | | Dan Bennett (360 Sprints - Winged) | 10th | - | 12th | - |
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| 9/22/2023 | Genesee Speedway - Batavia, NY Genesee Speedway $1,000-to-win 305 Sprints - Winged: CRSA Sprint Cars | Results | | Dan Bennett (305 Sprints - Winged) | 1st | - | - | 15th (DNF) |
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| 9/29/2023 | Fulton Speedway - Fulton, NY Milton CAT Outlaw Weekend Fast Friday 360 Sprints - Winged: Empire Super Sprints DIRTcar 358 Modifieds, DIRTcar Sportsman Modifieds | Results | | Dan Bennett (360 Sprints - Winged) | 6th | 5th | - | 22nd |
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