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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 | | Jack James (Winged Crate Sprints) | 4th | - | - | 3rd |
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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 |
| 5/25/2019 | 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 | | Jack James (Winged Crate Sprints) | 5th | - | - | 3rd |
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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 | | Jack James (Winged Crate Sprints) | 3rd | - | - | 3rd |
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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 | | Jack James (Winged Crate Sprints) | 4th | - | - | 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 | | Jack James (Winged Crate Sprints) | 2nd | - | - | 4th |
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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 | | Jack James (Winged Crate Sprints) | 6th | - | - | 4th |
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| 7/13/2019 | Plymouth Speedway - Plymouth, IN ILVDIRT Stock Car Throwdown at the Playground Night 2 DIRTcar UMP Modifieds, Super Sports, Winged Crate Sprints | Results | | Jack James (Winged Crate Sprints) | 1st | - | - | 1st |
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| 7/26/2019 | Gas City I-69 Speedway - Gas City, IN Great Lakes Sprints Night 360 Sprints - Winged: GLSS-Great Lakes Super Sprints Winged Outlaw, Non-Wing Outlaw | Results | | Jack James (360 Sprints - Winged) | 7th | - | - | 16th |
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| 8/10/2019 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Super Sports, Street Stocks, Winged Crate Sprints | Results | | Jack James (Winged Crate Sprints) | 4th | - | - | 3rd |
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| 8/21/2019 | Kokomo Speedway - Kokomo, IN 410 Sprints - Non-Winged: USAC National Sprint Cars 410 Sprints - Winged | Results | | Jack James (410 Sprints - Non-Winged) | 7th | - | - | - |
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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 | | Jack James (Winged Crate Sprints) | 4th | - | - | 4th |
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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 | | Jack James (Winged Crate Sprints) | 4th | - | - | 3rd |
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| 9/26/2019 | Gas City I-69 Speedway - Gas City, IN 410 Sprints - Non-Winged: USAC National Sprint Cars Winged Outlaw, Non-Wing Outlaw | Results | | Jack James (410 Sprints - Non-Winged) | 7th | - | 11th | - |
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| 9/28/2019 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: All Star Circuit of Champions Midgets: USAC National Midgets 410 Sprints - Non-Winged: USAC National Sprint Cars Silver Crown: USAC Silver Crown | Results | | Jack James (410 Sprints - Non-Winged) | 7th | - | 13th | - |
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