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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 | | Jacob Ruppe (Stock Non-Wing) | 3rd | - | - | 5th |
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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 | | Jacob Ruppe (Stock Non-Wing) | 2nd | - | - | 5th |
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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 | | Jacob Ruppe (Stock Non-Wing) | 3rd | - | - | 6th |
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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 | | Jacob Ruppe (Stock Non-Wing) | 4th | - | - | 6th |
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| 6/19/2020 | US 24 Speedway - Logansport, IN WEEKLY Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Senior Micros | Results | | Jacob Ruppe (Winged Outlaw) | - | - | - | - | | Jacob Ruppe (Non-Wing Outlaw) | 7th | - | - | 6th |
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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 | | Jacob Ruppe (Stock Non-Wing) | 4th | - | - | 12th |
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| 6/26/2020 | Plymouth Speedway - Plymouth, IN USAC National Sprint Series 410 Sprints - Non-Winged: USAC National Sprint Cars Asphalt Mini Stocks, Stock Non-Wing | Results | | Jacob Ruppe (Stock Non-Wing) | 7th | - | 4th | 14th |
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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 | | Jacob Ruppe (Stock Non-Wing) | 3rd | - | - | 14th |
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| 7/13/2020 | Miami County Raceway - Peru, IN Let's Race Monday! Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Hybrid 600cc Micros | Results | | Jacob Ruppe (Hybrid 600cc Micros) | 5th | - | - | 7th |
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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 | | Jacob Ruppe (Stock Non-Wing) | 7th | - | 1st | 16th |
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| 8/29/2020 | Miami County Raceway - Peru, IN Clarence Hoch Purple Heart Classic*** (Month of Money Race 1) Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Hybrid 600cc Micros | Results | | Jacob Ruppe (Winged A-Class) | 3rd | - | - | 3rd |
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| 9/5/2020 | US 24 Speedway - Logansport, IN 5th point night Paul Moyer Mem. NW $500 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Stock Non-Wing, Junior Sprints, Senior Micros | Results | | Jacob Ruppe (Non-Wing Outlaw) | 7th | - | 5th | 11th |
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