| | Heat | Dash | B Feature | A Feature |
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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 Kolwyck (Street Stocks) | 9th | - | 9th | - |
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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 Kolwyck (Street Stocks) | 2nd | - | - | 21st |
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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 | | Jacob Kolwyck (Street Stocks) | 4th | - | - | 2nd |
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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 Kolwyck (Street Stocks) | 5th | - | - | 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 | | Jacob Kolwyck (Street Stocks) | 3rd | - | - | 5th |
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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 Kolwyck (Street Stocks) | 5th | - | - | 12th |
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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 Kolwyck (Street Stocks) | 3rd | - | - | 20th |
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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 Kolwyck (Street Stocks) | 5th | - | - | 5th |
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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 Kolwyck (Street Stocks) | 3rd | - | - | 4th |
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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 | | Jacob Kolwyck (Street Stocks) | 3rd | - | - | 5th |
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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 | | Jacob Kolwyck (Street Stocks) | 2nd | - | - | 6th |
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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 Kolwyck (DIRTcar UMP Modifieds) | - | - | - | - | | Jacob Kolwyck (Street Stocks) | 3rd | - | - | 3rd |
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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 Kolwyck (Street Stocks) | 3rd | - | - | 13th |
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