| | Heat | Dash | B Feature | A Feature |
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| 4/26/2019 | Cottage Grove Speedway - Cottage Grove, OR SPRING FLING 360 Sprints - Winged, A Modifieds, B Modifieds | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 10th |
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| 5/3/2019 | Willamette Speedway - Lebanon, OR FAST FRIDAY! Super Sports, IMCA Sport Mods, Sportsman Sportsmans, Super Sports, B Modifieds | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 6th |
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| 5/26/2019 | Sunset Speedway Park - Banks, OR SPRING CHALLENGE/ARMED FORCES NIGHT ($5.00 GENERAL ADMISSION ALL MILITARY) A Modifieds, Restricted 'A' Class, Winged A-Class, B Modifieds, Street Stocks, Dwarf, Hornets | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 5th |
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| 5/31/2019 | Willamette Speedway - Lebanon, OR STRAWBERRY CUP - Late Models, IMCA Mods, IMCA Sport Mods, Sportsman, Hornets Dirt Super Late Models, Sportsmans, Dirt Mini Trucks, A Modifieds, B Modifieds | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 1st |
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| 6/1/2019 | Willamette Speedway - Lebanon, OR STRAWBERRY CUP - Late Models, Super Sports, IMCA Mods, IMCA Sport Mods, Street Stocks Dirt Super Late Models, Super Sports, A Modifieds, B Modifieds, Street Stocks | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 1st |
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| 6/15/2019 | Cottage Grove Speedway - Cottage Grove, OR DAD'S NIGHT - DADS FREE 360 Sprints - Non-Winged: (Duplicated) WSS-Wingless Sprint Series Dirt Super Late Models, A Modifieds, B Modifieds, Hornets | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 1st |
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| 6/21/2019 | Willamette Speedway - Lebanon, OR FAST FRIDAY! Karts, IMCA Sport Mods, Hornets Dirt Mini Trucks, A Modifieds, B Modifieds | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 1st |
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| 6/22/2019 | Cottage Grove Speedway - Cottage Grove, OR GRAD NIGHT - CLASS OF 2019 FREE Sportsman Sprints, B Modifieds, Street Stocks, Hornets | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 3rd |
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| 6/28/2019 | Willamette Speedway - Lebanon, OR Wild West Modified Shootout Speedweek Stock Cars, A Modifieds, B Modifieds | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 13th |
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| 6/29/2019 | Willamette Speedway - Lebanon, OR Wild West Modified Shootout Speedweek Stock Cars, A Modifieds, B Modifieds | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 2nd |
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| 7/4/2019 | Cottage Grove Speedway - Cottage Grove, OR FREEDOM CUP - FIREWORKS Sportsman Sprints, A Modifieds, B Modifieds | Results | | Skyler Winebarger (B Modifieds) | - | - | 6th | - |
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| 7/5/2019 | Cottage Grove Speedway - Cottage Grove, OR FREEDOM CUP PRESENTED BY HOPPES CONSTRUCTION Sportsman Sprints, A Modifieds, B Modifieds | Results | | Skyler Winebarger (B Modifieds) | - | - | 2nd | 7th |
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| 7/6/2019 | Cottage Grove Speedway - Cottage Grove, OR FREEDOM CUP PRESENTED BY HOPPES CONSTRUCTION Sportsman Sprints, A Modifieds, B Modifieds | Results | | Skyler Winebarger (B Modifieds) | - | - | 4th | 20th |
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| 7/13/2019 | Willamette Speedway - Lebanon, OR SHRINERS NIGHT Dirt Super Late Models, Stock Cars, Sportsmans, Super Sports, Dirt Mini Trucks, A Modifieds, B Modifieds, Street Stocks | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 8th |
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| 8/3/2019 | Willamette Speedway - Lebanon, OR Late Models, Super Sports, Sportsman, IMCA Mods, IMCA Sport Mods, Street Stocks, Hornets Dirt Super Late Models, Sportsmans, Super Sports, Dirt Mini Trucks, A Modifieds, B Modifieds, Street Stocks | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 7th |
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| 8/23/2019 | Cottage Grove Speedway - Cottage Grove, OR MODIFIED NATIONALS A Modifieds, B Modifieds | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 2nd |
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| 8/24/2019 | Cottage Grove Speedway - Cottage Grove, OR MODIFIED NATIONALS 360 Sprints - Winged, A Modifieds, B Modifieds | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 12th |
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| 8/31/2019 | Sunset Speedway Park - Banks, OR DOUG WALTERS MEMORIAL DIRTcar Factory Stock, Hobby Stocks, A Modifieds, Restricted 'A' Class, Winged A-Class, B Modifieds, Street Stocks, Dirt Late Models, Hornets, Asphalt Rookie Stocks | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 3rd |
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| 9/1/2019 | Sunset Speedway Park - Banks, OR DOUG WALTERS MEMORIAL (67 LAPS FOR LATE MODELS) DIRTcar Factory Stock, Hobby Stocks, A Modifieds, Restricted 'A' Class, Winged A-Class, B Modifieds, Street Stocks, Dirt Late Models, Hornets, Asphalt Rookie Stocks | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 1st |
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| 9/13/2019 | Cottage Grove Speedway - Cottage Grove, OR CHAMPIONSHIP NIGHT #1 Sportsman Sprints, Dirt Super Late Models, A Modifieds, B Modifieds, Street Stocks, Hornets | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 12th |
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| 9/14/2019 | Cottage Grove Speedway - Cottage Grove, OR CHAMPIONSHIP NIGHT FINALE Sportsman Sprints, Dirt Super Late Models, A Modifieds, B Modifieds, Street Stocks, Hornets | Results | | Skyler Winebarger (B Modifieds) | - | - | - | 12th |
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