| | Heat | Dash | B Feature | A Feature |
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| 1/8/1999 | Tulsa Expo Raceway - Tulsa, OK 13th Annual Chili Bowl Midgets | Results | | Sammy Swindell (Midgets) | 2nd | - | - | 3rd |
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| 1/9/1999 | Tulsa Expo Raceway - Tulsa, OK 13th Annual Chili Bowl Midgets | Results | | Sammy Swindell (Midgets) | - | - | - | 3rd |
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| 2/19/1999 | Kings Speedway - Hanford, CA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 2nd |
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| 2/20/1999 | Perris Auto Speedway - Perris, CA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 22nd |
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| 2/26/1999 | Manzanita Speedway - Phoenix, AZ 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 6th |
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| 2/27/1999 | Manzanita Speedway - Phoenix, AZ 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 3rd |
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| 3/26/1999 | Devil's Bowl Speedway - Mesquite, TX | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | 1st | 18th |
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| 4/2/1999 | Eldora Speedway - Rossburg, OH 360 Sprints - Winged: NRA Sprint Invaders 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 3rd |
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| 4/24/1999 | Devil's Bowl Speedway - Mesquite, TX 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 1st |
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| 4/30/1999 | Knoxville Raceway - Knoxville, IA | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | 1st | 14th |
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| 5/1/1999 | Knoxville Raceway - Knoxville, IA | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 1st |
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| 5/3/1999 | Huset's Speedway - Brandon, SD | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 6th |
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| 5/14/1999 | Missouri State Fair Speedway - Sedalia, MO 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 14th |
|
| 5/16/1999 | Tri-State Speedway - Haubstadt, IN 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 16th |
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| 5/19/1999 | Bloomington Speedway - Bloomington, IN 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 1st |
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| 5/22/1999 | Terre Haute Action Track - Terre Haute, IN 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | 1st | 4th |
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| 5/25/1999 | Lernerville Speedway - Sarver, PA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 7th |
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| 5/27/1999 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 6th |
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| 5/28/1999 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 5th |
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| 5/29/1999 | Hagerstown Speedway - Hagerstown, MD 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 23rd |
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| 5/30/1999 | Hagerstown Speedway - Hagerstown, MD 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 19th |
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| 6/5/1999 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 4th |
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| 6/19/1999 | Heartland Motorsports Park - Topeka, KS | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 13th |
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| 6/25/1999 | Eagle Raceway - Eagle, NE 360 Sprints - Winged, 410 Sprints - Winged | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 10th |
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| 6/26/1999 | Eagle Raceway - Eagle, NE 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 2nd |
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| 7/2/1999 | Knoxville Raceway - Knoxville, IA 360 Sprints - Winged, 410 Sprints - Winged | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 19th |
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| 7/3/1999 | Knoxville Raceway - Knoxville, IA | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 12th |
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| 7/4/1999 | Nebraska Raceway Park - Greenwood, NE 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 2nd |
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| 7/6/1999 | Huset's Speedway - Brandon, SD | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 15th |
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| 7/8/1999 | Red River Valley Speedway - West Fargo, ND 360 Sprints - Winged, 410 Sprints - Winged | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 3rd |
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| 7/9/1999 | Red River Valley Speedway - West Fargo, ND 360 Sprints - Winged, 410 Sprints - Winged | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 14th |
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| 7/10/1999 | Red River Valley Speedway - West Fargo, ND 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 21st |
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| 7/12/1999 | Cedar Lake Speedway - New Richmond, WI 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 2nd |
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| 7/15/1999 | Eldora Speedway - Rossburg, OH 360 Sprints - Winged: NRA Sprint Invaders 410 Sprints - Winged | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 4th |
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| 7/16/1999 | Eldora Speedway - Rossburg, OH | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 8th |
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| 7/17/1999 | Eldora Speedway - Rossburg, OH | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 1st |
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| 7/19/1999 | LaSalle Speedway - Lasalle, IL 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 5th |
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| 7/21/1999 | Knoxville Raceway - Knoxville, IA | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 22nd |
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| 7/23/1999 | Missouri State Fair Speedway - Sedalia, MO 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 5th |
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| 7/27/1999 | Lernerville Speedway - Sarver, PA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 4th |
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| 7/29/1999 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 5th |
|
| 7/30/1999 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 5th |
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| 7/31/1999 | Hagerstown Speedway - Hagerstown, MD 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 3rd |
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| 8/6/1999 | Eldora Speedway - Rossburg, OH | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 11th |
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| 8/7/1999 | Eldora Speedway - Rossburg, OH 360 Sprints - Winged: NRA Sprint Invaders 410 Sprints - Winged | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 14th |
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| 8/13/1999 | Knoxville Raceway - Knoxville, IA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 6th |
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| 8/14/1999 | Knoxville Raceway - Knoxville, IA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 10th |
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| 8/20/1999 | Grays Harbor Raceway - Elma, WA | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 1st |
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| 8/21/1999 | Grays Harbor Raceway - Elma, WA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 2nd |
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| 8/23/1999 | Cottage Grove Speedway - Cottage Grove, OR 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 5th |
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| 8/25/1999 | ZZZ Southern Oregon Speedway - Medford, OR 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 19th |
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| 8/27/1999 | San Jose Fairgrounds - San Jose, CA | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 6th |
|
| 8/28/1999 | San Jose Fairgrounds - San Jose, CA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 3rd |
|
| 9/3/1999 | Calistoga Speedway - Calistoga, CA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 1st |
|
| 9/4/1999 | Calistoga Speedway - Calistoga, CA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 4th |
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| 9/5/1999 | Calistoga Speedway - Calistoga, CA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 1st |
|
| 9/10/1999 | Kings Speedway - Hanford, CA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 2nd |
|
| 9/11/1999 | Santa Maria Speedway - Santa Maria, CA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 4th |
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| 9/16/1999 | Silver Dollar Speedway - Chico, CA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 2nd |
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| 9/18/1999 | Silver Dollar Speedway - Chico, CA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 22nd |
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| 9/21/1999 | Sweetwater Speedway - Rock Springs, WY 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 1st |
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| 9/24/1999 | Nebraska Raceway Park - Greenwood, NE | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 1st |
|
| 9/25/1999 | Nebraska Raceway Park - Greenwood, NE 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 1st |
|
| 10/1/1999 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 11th |
|
| 10/2/1999 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 27th |
|
| 10/15/1999 | Devil's Bowl Speedway - Mesquite, TX | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 11th |
|
| 10/22/1999 | Manzanita Speedway - Phoenix, AZ 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 6th |
|
| 10/23/1999 | Manzanita Speedway - Phoenix, AZ 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 4th |
|
| 10/30/1999 | Perris Auto Speedway - Perris, CA 410 Sprints - Winged: World of Outlaws | Results | | Sammy Swindell (410 Sprints - Winged) | - | - | - | 5th |
|