| | 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 | | Jeff Shearer (Dirt Super Late Models) | - | - | 10th | - |
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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 | | Jeff Shearer (Dirt Super Late Models) | - | - | 2nd | 19th |
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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 | | Jeff Shearer (Dirt Super Late Models) | 5th | - | - | 24th |
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| 4/24/1999 | Hagerstown Speedway - Hagerstown, MD Stanley Schetrompf Memorial - STARS Late Models + Regular Show Dirt Super Late Models, Factory Stocks, Dirt Late Models, Pure Stock | Results | | Jeff Shearer (Dirt Super Late Models) | - | - | 17th | - |
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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 | | Jeff Shearer (Dirt Super Late Models) | - | - | 6th | DNS |
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| 6/26/1999 | Hagerstown Speedway - Hagerstown, MD Regular Show + Enduro Dirt Super Late Models, Factory Stocks, Dirt Late Models, Enduro, Pure Stock | Results | | Jeff Shearer (Dirt Super Late Models) | - | - | 3rd | 24th |
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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 | | Jeff Shearer (Dirt Super Late Models) | - | - | 4th | 19th |
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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 | | Jeff Shearer (Dirt Super Late Models) | - | - | 8th | - |
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| 8/14/1999 | Hagerstown Speedway - Hagerstown, MD STARS - Late Models + 4C Dirt Super Late Models, Factory Stocks | Results | | Jeff Shearer (Dirt Super Late Models) | - | - | 13th | - |
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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 | | Jeff Shearer (Dirt Super Late Models) | - | - | 12th | - |
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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 | | Jeff Shearer (Dirt Super Late Models) | - | - | DNS | 18th |
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