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| 5/23/2020 | Plymouth Speedway - Plymouth, IN Cabin Fever - Saturday Night Event DIRTcar UMP Modifieds, Asphalt Mini Stocks, Super Sports, Stock Non-Wing, Street Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 3rd | - | - | 6th | | Dylan Woodling (Stock Non-Wing) | 2nd | - | - | 2nd |
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| 5/30/2020 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Asphalt Mini Stocks, Super Sports, Stock Non-Wing, Street Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 5th | - | 4th | 18th | | Dylan Woodling (Stock Non-Wing) | 1st | - | - | 1st |
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| 6/5/2020 | US 24 Speedway - Logansport, IN Rest class $300 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Senior Micros | Results | | Dylan Woodling (Non-Wing Outlaw) | 1st | - | - | - |
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| 6/6/2020 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Asphalt Mini Stocks, Super Sports, Stock Non-Wing, Street Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 5th | - | 6th | - | | Dylan Woodling (Stock Non-Wing) | 4th | - | - | 4th |
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| 6/13/2020 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Asphalt Mini Stocks, Super Sports, Stock Non-Wing, Street Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 3rd | - | - | 8th | | Dylan Woodling (Stock Non-Wing) | 1st | - | - | 2nd |
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| 6/20/2020 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Asphalt Mini Stocks, Super Sports, Stock Non-Wing, Street Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 3rd | - | - | 5th | | Dylan Woodling (Stock Non-Wing) | 1st | - | - | 2nd |
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| 6/24/2020 | Fairbury Speedway - Fairbury, IL June 24th 2020 DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 2nd | - | - | 9th |
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| 6/27/2020 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Super Sports, Street Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 6th | - | - | 6th |
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| 7/11/2020 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Asphalt Mini Stocks, Stock Non-Wing, Street Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 1st | - | - | 4th | | Dylan Woodling (Stock Non-Wing) | 2nd | - | - | 1st |
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| 7/18/2020 | Lincoln Park Speedway - Putnamville, IN Little Feet Bicycle Challenge #2 and FIREWORS DIRTcar UMP Modifieds, Factory Stocks, 410 Sprints - Non-Winged, Super Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 2nd | - | - | 4th |
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| 7/25/2020 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Super Sports, Stock Non-Wing, Street Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 2nd | - | - | 5th | | Dylan Woodling (Stock Non-Wing) | 3rd | - | - | 5th |
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| 8/8/2020 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Asphalt Mini Stocks, Super Sports, Stock Non-Wing, Street Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 1st | - | - | 5th | | Dylan Woodling (Stock Non-Wing) | 3rd | - | - | 2nd |
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| 8/15/2020 | Plymouth Speedway - Plymouth, IN 2020 Season Championship Night DIRTcar UMP Modifieds, Asphalt Mini Stocks, Super Sports, Stock Non-Wing, Street Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 1st | - | - | 2nd | | Dylan Woodling (Stock Non-Wing) | 1st | - | - | 9th |
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| 8/29/2020 | Lincoln Park Speedway - Putnamville, IN Little Bicycle Challenge #3 DIRTcar UMP Modifieds, Factory Stocks, 410 Sprints - Non-Winged, Super Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 3rd | - | - | 9th |
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| 9/5/2020 | Fairbury Speedway - Fairbury, IL Twin 10's FALS Super Nationals DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 3rd | - | 2nd | 15th |
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| 9/12/2020 | Lincoln Park Speedway - Putnamville, IN The Gary Rickett's Memorial - Buckeye Bob 33 410 Sprints - Non-Winged: USAC National Sprint Cars DIRTcar UMP Modifieds, Factory Stocks, Super Stocks | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 4th | - | - | 8th |
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| 9/15/2020 | Fairbury Speedway - Fairbury, IL "One for the Road" Late Model Special DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Dylan Woodling (DIRTcar UMP Modifieds) | 5th | - | 1st | 9th |
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| 10/17/2020 | Kokomo Speedway - Kokomo, IN Kokomo KlashXIV Dirt Super Late Models, Hobby Stocks, A Modifieds, Street Stocks, Hornets, Super Stocks | Results | | Dylan Woodling (A Modifieds) | - | - | - | - |
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