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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 | | Roy Deese Jr (Dirt Super Late Models) | 1st | - | - | 1st |
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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 | | Roy Deese Jr (Dirt Super Late Models) | 2nd | - | - | 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 | | Roy Deese Jr (Dirt Super Late Models) | 2nd | - | - | 5th |
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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 | | Roy Deese Jr (Dirt Super Late Models) | 1st | - | - | 11th |
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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 | | Roy Deese Jr (Dirt Super Late Models) | 2nd | - | - | 3rd |
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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 | | Roy Deese Jr (Dirt Super Late Models) | 4th | - | - | 10th |
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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 | | Roy Deese Jr (Dirt Super Late Models) | 2nd | - | - | 3rd |
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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 | | Roy Deese Jr (Dirt Super Late Models) | 1st | - | - | 7th |
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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 | | Roy Deese Jr (Dirt Super Late Models) | 1st | - | - | 17th |
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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 | | Roy Deese Jr (Dirt Super Late Models) | 3rd | - | - | 6th |
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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 | | Roy Deese Jr (Dirt Super Late Models) | 4th | - | - | 20th |
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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 | | Roy Deese Jr (Dirt Super Late Models) | 1st | - | - | 6th |
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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 | | Roy Deese Jr (Dirt Super Late Models) | 3rd | - | - | 4th |
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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 | | Roy Deese Jr (Dirt Super Late Models) | - | - | 12th | 12th |
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| 8/14/1999 | Hagerstown Speedway - Hagerstown, MD STARS - Late Models + 4C Dirt Super Late Models, Factory Stocks | Results | | Roy Deese Jr (Dirt Super Late Models) | 2nd | 1st | - | 4th |
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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 | | Roy Deese Jr (Dirt Super Late Models) | 1st | - | - | 4th |
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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 | | Roy Deese Jr (Dirt Super Late Models) | 4th | - | - | 2nd |
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| 10/3/1999 | Hagerstown Speedway - Hagerstown, MD 14TH ANNUAL MCBEE MEMORIAL + SUPER SPORTSMAN Sportsman Sprints, Dirt Super Late Models | Results | | Roy Deese Jr (Dirt Super Late Models) | 2nd | - | - | 4th |
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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 | | Roy Deese Jr (Dirt Super Late Models) | 2nd | - | - | 31st |
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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 | | Roy Deese Jr (Dirt Super Late Models) | 2nd | - | - | 3rd |
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