| | Heat | Dash | B Feature | A Feature |
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| 3/27/1999 | Hagerstown Speedway - Hagerstown, MD Season Opener Dirt Super Late Models, Dirt Big Block Modifieds, DIRTcar 358 Modifieds | Results | | Kenny Pettyjohn (Dirt Big Block Modifieds) | - | - | 4th | 12th |
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| 6/19/1999 | Hagerstown Speedway - Hagerstown, MD Regular Show Dirt Super Late Models, Factory Stocks, Dirt Late Models, Pure Stock | Results | | Kenny Pettyjohn (Dirt Super Late Models) | 3rd | - | - | 8th |
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| 8/13/1999 | Hagerstown Speedway - Hagerstown, MD MACS - Late Models + LMS & PS Dirt Super Late Models, Dirt Late Models, Pure Stock | Results | | Kenny Pettyjohn (Dirt Super Late Models) | 4th | - | 9th | 9th |
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| 9/12/1999 | Hagerstown Speedway - Hagerstown, MD Regular Show + Fall Championship Enduro Dirt Super Late Models, Factory Stocks, Dirt Late Models, Enduro, Pure Stock | Results | | Kenny Pettyjohn (Dirt Super Late Models) | 4th | - | - | 12th |
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| 9/19/1999 | Hagerstown Speedway - Hagerstown, MD Richard Bonebrake Memorial - Super Late Models + Regular Show Dirt Super Late Models, Factory Stocks, Dirt Late Models, Pure Stock | Results | | Kenny Pettyjohn (Dirt Super Late Models) | - | - | 1st | 19th |
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| 10/3/1999 | Hagerstown Speedway - Hagerstown, MD 14TH ANNUAL MCBEE MEMORIAL + SUPER SPORTSMAN Sportsman Sprints, Dirt Super Late Models | Results | | Kenny Pettyjohn (Dirt Super Late Models) | 4th | - | - | 5th |
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| 10/23/1999 | Hagerstown Speedway - Hagerstown, MD HUB CITY NATIONAL Dirt Super Late Models, Factory Stocks, Dirt Late Models, Pure Stock | Results | | Kenny Pettyjohn (Dirt Super Late Models) | - | - | 10th | 21st |
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| 10/31/1999 | Hagerstown Speedway - Hagerstown, MD 410 Sprints - Winged, Dirt Super Late Models, Dirt Big Block Modifieds, DIRTcar 358 Modifieds | Results | | Kenny Pettyjohn (Dirt Super Late Models) | 5th | - | - | 8th | | Kenny Pettyjohn (Dirt Big Block Modifieds) | - | - | 5th | - |
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