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| 4/15/2023 | Wayne County Speedway - Orrville, OH 410 Sprints - Winged: FASTonDIRT Dirt Super Late Models, DIRTcar UMP Modifieds, Super Stocks, Dirt Mini Stocks | Results | | J.R. Gentry (Dirt Super Late Models) | 3rd | - | - | 2nd |
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| 5/6/2023 | Wayne County Speedway - Orrville, OH BOSS Buckeye Outlaw Sprint Series 410 Sprints - Non-Winged: BOSS Buckeye Outlaw Sprint Series Dirt Super Late Models, DIRTcar UMP Modifieds, Super Stocks, Dirt Mini Stocks | Results | | J.R. Gentry (Dirt Super Late Models) | 4th | - | - | 3rd |
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| 5/13/2023 | Wayne County Speedway - Orrville, OH 410 Sprints - Winged, Dirt Super Late Models, DIRTcar UMP Modifieds, Super Stocks, Dirt Mini Stocks | Results | | J.R. Gentry (Dirt Super Late Models) | 1st | - | - | 2nd |
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| 5/20/2023 | Wayne County Speedway - Orrville, OH White's Ford Night: Fast 5 Regular Show 410 Sprints - Winged, Dirt Super Late Models, DIRTcar UMP Modifieds, Super Stocks, Dirt Mini Stocks | Results | | J.R. Gentry (Dirt Super Late Models) | 2nd | - | - | 1st |
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| 5/27/2023 | Wayne County Speedway - Orrville, OH 410 Sprints - Winged, Dirt Super Late Models, DIRTcar UMP Modifieds, Super Stocks, Dirt Mini Stocks | Results | | J.R. Gentry (Dirt Super Late Models) | 3rd | - | - | 2nd |
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| 6/3/2023 | Wayne County Speedway - Orrville, OH Fast 5 Regular Show 410 Sprints - Winged, Dirt Super Late Models, DIRTcar UMP Modifieds, Super Stocks, Dirt Mini Stocks | Results | | J.R. Gentry (Dirt Super Late Models) | 2nd | - | - | 1st |
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| 6/17/2023 | Wayne County Speedway - Orrville, OH Weekly Racing Mod Lites: United CC Modified Series Dirt Super Late Models, DIRTcar UMP Modifieds, Super Stocks, Dirt Mini Stocks | Results | | J.R. Gentry (Dirt Super Late Models) | 4th | - | - | 1st |
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| 6/24/2023 | Wayne County Speedway - Orrville, OH FAST Sprint Series 410 Sprints - Winged: FASTonDIRT Dirt Super Late Models, DIRTcar UMP Modifieds, Super Stocks, Dirt Mini Stocks | Results | | J.R. Gentry (Dirt Super Late Models) | 1st | - | - | 11th |
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| 7/7/2023 | Hilltop Speedway - Millersburg, OH Dirt Super Late Models: Iron-Man Late Model Series Mod Lites: United CC Modified Series | Results | | J.R. Gentry (Dirt Super Late Models) | 6th | - | 1st | 17th |
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| 7/16/2023 | Wayne County Speedway - Orrville, OH DIRTcar Summer Nationals DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Super Stocks, Dirt Mini Stocks | Results | | J.R. Gentry (DIRTcar Late Models) | 5th | - | 10th | 13th |
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| 7/22/2023 | Wayne County Speedway - Orrville, OH FAST 410 Sprint Series 410 Sprints - Winged: FASTonDIRT Dirt Super Late Models, DIRTcar UMP Modifieds, Super Stocks, Dirt Mini Stocks | Results | | J.R. Gentry (Dirt Super Late Models) | 2nd | - | - | 8th |
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| 7/29/2023 | Wayne County Speedway - Orrville, OH Santmyer Energy Night - Fast 5 Regular Show 410 Sprints - Winged, Dirt Super Late Models, DIRTcar UMP Modifieds, Super Stocks, Dirt Mini Stocks | Results | | J.R. Gentry (Dirt Super Late Models) | 3rd | - | - | 3rd |
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| 8/5/2023 | Wayne County Speedway - Orrville, OH Fast 5 Regular Show 410 Sprints - Winged, Dirt Super Late Models, DIRTcar UMP Modifieds, Super Stocks, Dirt Mini Stocks | Results | | J.R. Gentry (Dirt Super Late Models) | 2nd | 3rd | - | 1st |
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| 8/12/2023 | Wayne County Speedway - Orrville, OH Kids Night + Danny Gardner Memorial 410 Sprints - Winged, Dirt Super Late Models, DIRTcar UMP Modifieds, Super Stocks, Dirt Mini Stocks | Rain Out |
| 8/19/2023 | Wayne County Speedway - Orrville, OH BOSS Sprint Series 410 Sprints - Non-Winged: BOSS Buckeye Outlaw Sprint Series 410 Sprints - Winged, Dirt Super Late Models, DIRTcar UMP Modifieds, Super Stocks, Dirt Mini Stocks | Results | | J.R. Gentry (Dirt Super Late Models) | 2nd | - | - | 17th (DNF) |
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| 8/26/2023 | Wayne County Speedway - Orrville, OH Season Championship - Fast 5 Regular Show 410 Sprints - Winged, Dirt Super Late Models, DIRTcar UMP Modifieds, Super Stocks, Dirt Mini Stocks | Results | | J.R. Gentry (Dirt Super Late Models) | 1st | - | - | 11th |
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| 9/3/2023 | Wayne County Speedway - Orrville, OH FAST 410 Sprint Cars 410 Sprints - Winged: FASTonDIRT 305 Sprints - Winged, Dirt Super Late Models, DIRTcar UMP Modifieds, Super Stocks | Results | | J.R. Gentry (Dirt Super Late Models) | 4th | - | - | 16th (DNF) |
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| 9/30/2023 | Wayne County Speedway - Orrville, OH Ohio Dirt Blowout - Night #2 410 Sprints - Winged, Dirt Super Late Models, DIRTcar UMP Modifieds, Super Stocks, Dirt Mini Stocks | Results | | J.R. Gentry (Dirt Super Late Models) | 2nd | - | - | 19th (DNF) |
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