| | 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 | | Les Hare (Dirt Super Late Models) | 1st | - | - | - |
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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 | | Les Hare (Dirt Super Late Models) | 4th | - | - | 8th |
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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 | | Les Hare (Dirt Super Late Models) | - | - | 2nd | 25th |
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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 | | Les Hare (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 | | Les Hare (Dirt Super Late Models) | 4th | - | - | 11th |
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| 7/3/1999 | Hagerstown Speedway - Hagerstown, MD Johnny Roberts Memorial Dirt Super Late Models, Factory Stocks, Dirt Late Models, Pure Stock | Results | | Les Hare (Dirt Super Late Models) | 5th | - | - | 21st |
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| 7/9/1999 | Hagerstown Speedway - Hagerstown, MD Conococheague 100 - STARS Dirt Super Late Models, Factory Stocks, Dirt Late Models, Pure Stock | Results | | Les Hare (Dirt Super Late Models) | - | - | DNS | - |
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| 7/24/1999 | Hagerstown Speedway - Hagerstown, MD Tony Armel Memorial - Late Model Sportsman + Regular Show & Enduro Dirt Super Late Models, Factory Stocks, Dirt Late Models, Enduro, Pure Stock | Results | | Les Hare (Dirt Super Late Models) | 6th | - | - | 10th |
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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 | | Les Hare (Dirt Super Late Models) | - | - | 16th | 16th |
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| 8/14/1999 | Hagerstown Speedway - Hagerstown, MD STARS - Late Models + 4C Dirt Super Late Models, Factory Stocks | Results | | Les Hare (Dirt Super Late Models) | 2nd | - | - | 20th |
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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 | | Les Hare (Dirt Super Late Models) | - | - | 2nd | 21st |
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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 | | Les Hare (Dirt Super Late Models) | - | - | 25th | - |
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