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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 Kolwyck (Street Stocks) | - | - | - | - |
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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 Kolwyck (Street Stocks) | 7th | - | - | - |
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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 Kolwyck (Street Stocks) | 6th | - | - | 4th |
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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 Kolwyck (Street Stocks) | 4th | - | - | 7th |
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| 6/27/2020 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Super Sports, Street Stocks | Results | | Jacob Kolwyck (Street Stocks) | 3rd | - | - | 19th |
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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 Kolwyck (Street Stocks) | 4th | - | - | 15th |
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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 Kolwyck (Street Stocks) | 5th | - | - | 6th |
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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 | | Jacob Kolwyck (Street Stocks) | 3rd | - | - | 4th |
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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 | | Jacob Kolwyck (Street Stocks) | 3rd | - | - | 9th |
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| 8/22/2020 | Plymouth Speedway - Plymouth, IN $5,000 to win 410 Sprints - Winged: All Star Circuit of Champions Asphalt Mini Stocks, Street Stocks | Results | | Jacob Kolwyck (Street Stocks) | - | - | - | 5th |
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| 10/16/2020 | Kokomo Speedway - Kokomo, IN Kokomo KlashXIV 305 Sprints - Winged, Midgets, Hobby Stocks, 410 Sprints - Non-Winged | Results | | Jacob Kolwyck (Hobby Stocks) | - | - | - | - |
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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 | | Jacob Kolwyck (Street Stocks) | - | - | - | - |
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