| | Heat | Dash | B Feature | A Feature |
|---|
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|---|
| 4/14/1999 | Bloomington Speedway - Bloomington, IN 410 Sprints - Winged: World of Outlaws | Results | | Gerald Cressman (410 Sprints - Winged) | - | - | 10th | - |
|
| 4/24/1999 | Jackson Motorplex - Jackson, MN | Results | | Gerald Cressman (360 Sprints - Winged) | - | - | - | 8th |
|
| 5/9/1999 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, 410 Sprints - Winged | Results | | Gerald Cressman (410 Sprints - Winged) | - | - | - | 10th |
|
| 5/16/1999 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, 410 Sprints - Winged | Results | | Gerald Cressman (410 Sprints - Winged) | - | - | - | 11th |
|
| 5/23/1999 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, 410 Sprints - Winged | Results | | Gerald Cressman (410 Sprints - Winged) | - | - | - | 19th |
|
| 6/6/1999 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, 410 Sprints - Winged | Results | | Gerald Cressman (410 Sprints - Winged) | - | - | - | 11th |
|
| 6/13/1999 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, 410 Sprints - Winged | Results | | Gerald Cressman (410 Sprints - Winged) | - | - | - | 15th |
|
| 6/20/1999 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, 410 Sprints - Winged | Results | | Gerald Cressman (410 Sprints - Winged) | - | - | - | - |
|
| 6/27/1999 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, 410 Sprints - Winged | Results | | Gerald Cressman (410 Sprints - Winged) | - | - | - | 16th |
|
| 7/4/1999 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, 410 Sprints - Winged | Results | | Gerald Cressman (410 Sprints - Winged) | - | - | - | 8th |
|
| 7/10/1999 | Red River Valley Speedway - West Fargo, ND 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged | Results | | Gerald Cressman (360 Sprints - Winged) | - | - | - | 11th |
|
| 7/18/1999 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, 410 Sprints - Winged | Results | | Gerald Cressman (410 Sprints - Winged) | - | - | - | 18th |
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| 8/11/1999 | Knoxville Raceway - Knoxville, IA | Results | | Gerald Cressman (410 Sprints - Winged) | - | - | - | - |
|
| 8/13/1999 | Knoxville Raceway - Knoxville, IA 410 Sprints - Winged: World of Outlaws | Results | | Gerald Cressman (410 Sprints - Winged) | - | - | - | - |
|
| 8/14/1999 | Knoxville Raceway - Knoxville, IA 410 Sprints - Winged: World of Outlaws | Results | | Gerald Cressman (410 Sprints - Winged) | - | - | - | - |
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