| | 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 | | Harold Dorsey Jr (Dirt Super Late Models) | - | - | 4th | - |
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| 3/28/1999 | Hagerstown Speedway - Hagerstown, MD Regular Show Dirt Super Late Models, Factory Stocks, Dirt Late Models, Pure Stock | Results | | Harold Dorsey Jr (Dirt Super Late Models) | - | - | 12th | - |
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| 4/17/1999 | Hagerstown Speedway - Hagerstown, MD Regular Show + Enduro Dirt Super Late Models, Factory Stocks, Dirt Late Models, Enduro, Pure Stock | Results | | Harold Dorsey Jr (Dirt Super Late Models) | 3rd | - | - | 16th |
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| 5/1/1999 | Hagerstown Speedway - Hagerstown, MD MACS Late Models + Spring Championship LMS/PS/4C Dirt Super Late Models, Factory Stocks, Dirt Late Models, Pure Stock | Results | | Harold Dorsey Jr (Dirt Super Late Models) | - | - | - | - |
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| 5/15/1999 | Hagerstown Speedway - Hagerstown, MD Regular Show Dirt Super Late Models, Factory Stocks, Dirt Late Models, Pure Stock | Results | | Harold Dorsey Jr (Dirt Super Late Models) | - | - | 13th | - |
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| 6/5/1999 | Hagerstown Speedway - Hagerstown, MD Regular Show + Enduro Dirt Super Late Models, Factory Stocks, Dirt Late Models, Enduro, Pure Stock | Results | | Harold Dorsey Jr (Dirt Super Late Models) | - | - | 5th | DNS |
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| 8/7/1999 | Hagerstown Speedway - Hagerstown, MD Regular Show + Enduro Dirt Super Late Models, Factory Stocks, Dirt Late Models, Enduro, Pure Stock | Results | | Harold Dorsey Jr (Dirt Super Late Models) | - | - | 3rd | 21st |
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| 8/14/1999 | Hagerstown Speedway - Hagerstown, MD STARS - Late Models + 4C Dirt Super Late Models, Factory Stocks | Results | | Harold Dorsey Jr (Dirt Super Late Models) | - | - | 14th | - |
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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 | | Harold Dorsey Jr (Dirt Super Late Models) | - | - | 6th | - |
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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 | | Harold Dorsey Jr (Dirt Super Late Models) | - | - | 7th | - |
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