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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 | | Jacob Ruppe (Stock Non-Wing) | 3rd | - | - | 8th |
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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 | Plymouth Speedway - Plymouth, IN DIRTcar UMP Modifieds, Super Sports, Stock Non-Wing, Street Stocks | Results | | Jacob Ruppe (Stock Non-Wing) | 6th | - | 1st | 8th |
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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 | | Jacob Ruppe (Stock Non-Wing) | 1st | - | - | 4th |
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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 | | Jacob Ruppe (Stock Non-Wing) | 4th | - | - | 11th |
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| 6/22/2019 | Plymouth Speedway - Plymouth, IN Saturday Night Event Featuring Outlaw Super Street Challenge DIRTcar UMP Modifieds, Super Sports, Stock Non-Wing, Winged Crate Sprints | Results | | Jacob Ruppe (Stock Non-Wing) | 4th | - | - | 9th |
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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 | | Jacob Ruppe (Non-Wing Outlaw) | 4th | - | - | 16th (DNF) |
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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 | | Jacob Ruppe (Stock Non-Wing) | 5th | - | 2nd | 16th |
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| 7/6/2019 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Stock Non-Wing, Street Stocks, Winged Crate Sprints | Results | | Jacob Ruppe (Stock Non-Wing) | 1st | - | - | 3rd |
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| 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 | | Jacob Ruppe (Stock Non-Wing) | 3rd | - | - | 4th |
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| 7/27/2019 | Plymouth Speedway - Plymouth, IN Saturday Night Event Featuring Sprints On Dirt Sprint Car Series 360 Sprints - Winged: SOD-Sprints On Dirt (360s) 410 Sprints - Winged, DIRTcar UMP Modifieds, Super Sports, Stock Non-Wing, Street Stocks, Winged Crate Sprints | Results | | Jacob Ruppe (Stock Non-Wing) | 2nd | - | - | 13th |
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| 8/3/2019 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Stock Non-Wing, Street Stocks, Winged Crate Sprints | Results | | Jacob Ruppe (Stock Non-Wing) | 2nd | - | - | 1st |
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| 8/24/2019 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Super Sports, Stock Non-Wing, Winged Crate Sprints | Results | | Jacob Ruppe (Stock Non-Wing) | 6th | - | - | 4th |
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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 | | Jacob Ruppe (Stock Non-Wing) | 2nd | - | - | 15th |
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| 9/14/2019 | Plymouth Speedway - Plymouth, IN Season Championship DIRTcar UMP Modifieds, Super Sports, Stock Non-Wing, Street Stocks, Winged Crate Sprints | Results | | Jacob Ruppe (Stock Non-Wing) | 1st | - | - | 3rd |
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| 10/5/2019 | Plymouth Speedway - Plymouth, IN Fall Wing Fling - 410 vs 360 plus n/w 600's & FWD 410 Sprints - Winged, Asphalt Mini Stocks, Stock Non-Wing | Results | | Jacob Ruppe (Stock Non-Wing) | - | - | - | - |
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