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| 4/6/2019 | Lincoln Park Speedway - Putnamville, IN Indiana Open Wheel.com Racing Fest with Fireworks DIRTcar UMP Modifieds, Factory Stocks, 410 Sprints - Non-Winged, Super Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 1st | - | - | 1st |
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| 4/20/2019 | US 24 Speedway - Logansport, IN 1st race of the season Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Dylan Woodling (Non-Wing Outlaw) | 4th | - | - | 17th (DNF) |
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| 5/4/2019 | Plymouth Speedway - Plymouth, IN Cabin Fever DIRTcar UMP Modifieds, Super Sports, Stock Non-Wing, Street Stocks, Winged Crate Sprints | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 2nd | - | - | 5th | | Dylan Woodling (Stock Non-Wing) | 1st | - | - | 1st |
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| 5/10/2019 | Paragon Speedway - Paragon, IN Season Opener DIRTcar UMP Modifieds, Stock Cars, 410 Sprints - Non-Winged, Hornets, Super Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 2nd | - | - | 11th |
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| 5/11/2019 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Stock Non-Wing, Street Stocks, Winged Crate Sprints | Rain Out |
| 5/18/2019 | Eldora Speedway - Rossburg, OH 360 Sprints - Winged: NRA Sprint Invaders DIRTcar UMP Modifieds, Stock Cars | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 3rd | - | - | 1st |
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| 5/25/2019 | Plymouth Speedway - Plymouth, IN Saturday Night Event Featuring Crate Sprint Cars DIRTcar UMP Modifieds, Super Sports, Street Stocks, Winged Crate Sprints, Dirt Crate Late Models | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 3rd | - | - | 4th |
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| 6/1/2019 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Super Sports, Stock Non-Wing, Winged Crate Sprints | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 1st | - | - | 4th | | Dylan Woodling (Stock Non-Wing) | 2nd | - | - | 1st |
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| 6/8/2019 | Plymouth Speedway - Plymouth, IN Battle of Borders Night 2 360 Sprints - Winged: GLSS-Great Lakes Super Sprints DIRTcar UMP Modifieds, Stock Non-Wing, Street Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 1st | - | - | 4th | | Dylan Woodling (Stock Non-Wing) | 4th | - | - | 1st |
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| 6/24/2019 | Miami County Raceway - Peru, IN Micros on the Midway. (Jr, Rest, and A Racing NW!) Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros | Results | | Dylan Woodling (Non-Wing Outlaw) | DNS | - | 4th | - |
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| 6/29/2019 | Plymouth Speedway - Plymouth, IN Mid Season Championship plus fireworks DIRTcar UMP Modifieds, Super Sports, Stock Non-Wing, Street Stocks, Winged Crate Sprints | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 3rd | - | - | 4th | | Dylan Woodling (Stock Non-Wing) | 1st | - | - | 2nd |
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| 7/6/2019 | Fairbury Speedway - Fairbury, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi National Midgets DIRTcar Late Models, DIRTcar UMP Modifieds | Rain Out |
| 7/12/2019 | Plymouth Speedway - Plymouth, IN ILVDIRT Stock Car Throwdown at the Playground Night 1 Asphalt Mini Stocks, Super Sports, Stock Non-Wing, Street Stocks | Results | | Dylan Woodling (Stock Non-Wing) | 3rd | - | - | 5th |
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| 8/3/2019 | Eldora Speedway - Rossburg, OH Family Fireworks Night by Casey's General Store DIRTcar UMP Modifieds, Stock Cars, Sport Compact | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 3rd | - | - | 7th |
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| 8/17/2019 | Plymouth Speedway - Plymouth, IN $5,000 to win 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds, Street Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 1st | - | - | 3rd |
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| 8/31/2019 | Miami County Raceway - Peru, IN Points Race #9 - "Honoring Our Military" Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Dylan Woodling (Non-Wing Outlaw) | 3rd | - | 7th | - |
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| 9/1/2019 | Eldora Speedway - Rossburg, OH Baltes Classic DIRTcar Late Models, DIRTcar UMP Modifieds, Stock Cars | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 5th | - | 1st | 5th |
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| 9/7/2019 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Super Sports, Stock Non-Wing, Street Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 2nd | - | - | 2nd | | Dylan Woodling (Stock Non-Wing) | 1st | - | - | 1st |
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| 9/21/2019 | Miami County Raceway - Peru, IN Sam Davis Memorial + Senior Shuffle! $500 to Win Senior Class! (Jr, Rest, and A Racing NW) Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Dylan Woodling (Non-Wing Outlaw) | 2nd | - | - | 14th |
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| 10/4/2019 | Federated Auto Parts I-55 Raceway - Pevely, MO DIRTcar Fall Nationals DIRTcar UMP Modifieds, Factory Stocks, B Modifieds, Pro Late Model | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 2nd | - | - | 16th |
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| 10/5/2019 | Federated Auto Parts I-55 Raceway - Pevely, MO DIRTcar Fall Nationals DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, B Modifieds | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | - | - | 2nd | 15th |
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| 10/19/2019 | Kokomo Speedway - Kokomo, IN Kokomo Klash XIII A Modifieds, Street Stocks, Dirt Late Models, Hornets, Super Stocks | Results | | Dylan Woodling (A Modifieds) | 1st | - | - | 5th |
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