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| 5/17/2019 | Southern Oklahoma Speedway - Ardmore, OK Friday Night Special Hobby Stocks, A Modifieds, Dirt Late Models, Non-Winged Sprints, 600cc Modifieds | Results | | Jerry Winters (Dirt Late Models) | 2nd | - | - | 5th |
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| 6/1/2019 | Enid Speedway - Enid, OK Late Models Dirt Late Models | Results | | Jerry Winters (Dirt Late Models) | 5th | - | 5th | 16th |
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| 6/21/2019 | Humboldt Speedway - Humboldt, KS $1000 to win Late Models Dirt Super Late Models, Factory Stocks, Midwest Modifieds, B Modifieds, Sport Compact | Results | | Jerry Winters (Dirt Super Late Models) | 3rd | - | - | 9th (DNF) |
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| 6/22/2019 | Caney Valley Speedway - Caney, KS Modifieds Dirt Super Late Models, DIRTcar UMP Modifieds, Factory Stocks, Stock Cars, USRA B-Mods | Results | | Jerry Winters (Dirt Super Late Models) | 4th | - | - | 8th (DNF) |
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| 6/29/2019 | Caney Valley Speedway - Caney, KS Weekly Race w/ Late Models Dirt Super Late Models, Factory Stocks, Stock Cars, B Modifieds, USRA B-Mods | Results | | Jerry Winters (Dirt Super Late Models) | 2nd | - | - | 12th |
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| 7/5/2019 | Longdale Speedway - Longdale, OK 5th Annual "America Proud" 4th of July Celebration featuring DIRT LATE MODELS! Dirt Super Late Models: Lucas Oil MLRA Stock Cars, A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Limited Sport Mod | Results | | Jerry Winters (Dirt Super Late Models) | 3rd | - | - | 23rd | | Jerry Winters (Dirt Late Models) | 3rd | - | - | 23rd |
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| 7/13/2019 | Caney Valley Speedway - Caney, KS Weekly Race W/ Late Models Dirt Super Late Models, Factory Stocks, Stock Cars, USRA B-Mods | Results | | Jerry Winters (Dirt Super Late Models) | 6th | - | - | 9th |
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| 7/20/2019 | Caney Valley Speedway - Caney, KS Weekly Race Dirt Super Late Models, Factory Stocks, Stock Cars, B Modifieds, USRA B-Mods | Results | | Jerry Winters (Dirt Super Late Models) | 2nd | - | - | 7th |
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| 8/10/2019 | Caney Valley Speedway - Caney, KS Weekly Race w/ Late Models Dirt Super Late Models, Factory Stocks, Stock Cars, B Modifieds, USRA B-Mods | Results | | Jerry Winters (Dirt Super Late Models) | 1st | - | - | 3rd |
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| 8/24/2019 | Oklahoma Sports Park - Ada, OK Sooner Late Model Series + Pure Stock, EMod, EMod Jr., Sport Mod Dirt Super Late Models, DIRTcar Factory Stock, B Modifieds, Asphalt Sport Mods, Limited Sport Mod | Results | | Jerry Winters (Dirt Super Late Models) | 1st | - | - | 3rd |
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| 8/31/2019 | Batesville Motor Speedway - Locust Grove, AR Arkansas Mini Stock Nationals Night Two Hobby Stocks, A Modifieds, Dirt Late Models | Results | | Jerry Winters (Dirt Late Models) | - | - | - | 5th |
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| 9/7/2019 | Caney Valley Speedway - Caney, KS Non-Winged Sprints: United Sprint League Dirt Super Late Models, Factory Stocks, Stock Cars, USRA B-Mods | Results | | Jerry Winters (Dirt Super Late Models) | 2nd | - | - | 6th |
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| 10/12/2019 | Caney Valley Speedway - Caney, KS Weekly Race w/ Late Models Dirt Super Late Models, Factory Stocks, Stock Cars, B Modifieds, USRA B-Mods | Results | | Jerry Winters (Dirt Super Late Models) | 1st | - | - | 2nd |
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| 10/19/2019 | Red Dirt Raceway - Meeker, OK 6th Annual Mark Robinson Memorial Dirt Super Late Models: Sooner Late Model Series Pure Stock: Western Outlaw Pure Stock Series Asphalt Mini Stocks, Hornets, 600cc Modifieds, Limited Sport Mod, Sportsman Micros | Results | | Jerry Winters (Dirt Super Late Models) | 5th | - | - | 14th |
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