| | Heat | Dash | B Feature | A Feature |
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| 5/26/2014 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks, 360 Sprints - Non-Winged | Results | | Greg Gunderson (Winged Outlaw) | 1st | - | - | 5th |
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| 6/14/2014 | Renegade Speedway - Canby, MN Micro Sprint Car Racing Winged A-Class: Miniakota Micro Sprint Series Generic 1 | Rain Out |
| 6/15/2014 | Huset's Speedway - Brandon, SD 360 Sprints - Winged: Minnesota Mafia 410 Sprints - Winged, Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks, 360 Sprints - Non-Winged | Rain Out |
| 6/29/2014 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, 410 Sprints - Winged, Hobby Stocks, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks | Results | | Greg Gunderson (Winged Outlaw) | 4th | - | - | 10th | | Greg Gunderson (Winged A-Class) | - | - | - | - |
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| 7/2/2014 | Huset's Speedway - Brandon, SD 410 Sprints - Winged: World of Outlaws Winged Outlaw, Winged A-Class, Street Stocks | Results | | Greg Gunderson (Winged Outlaw) | 4th | - | - | 2nd |
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| 7/3/2014 | Huset's Speedway - Brandon, SD July 3 Special - Outlaw Sprints & Fireworks! 410 Sprints - Winged, Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks | Results | | Greg Gunderson (Winged Outlaw) | 1st | - | - | 2nd |
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| 7/5/2014 | Angell Park Speedway - Sun Prairie, WI Midgets: USAC National Midgets with POWRi Winged A-Class: Badger 600 Winged Micros Winged Outlaw | Results | | Greg Gunderson (Winged A-Class) | - | - | - | - |
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| 7/5/2014 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Mid-Season Championship Restricted 'A' Class, Winged A-Class | Results | | Greg Gunderson (Winged A-Class) | - | - | - | - |
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| 7/6/2014 | Angell Park Speedway - Sun Prairie, WI Midgets: USAC National Midgets with POWRi Winged A-Class: Badger 600 Winged Micros Winged Outlaw | Results | | Greg Gunderson (Winged A-Class) | - | - | - | - |
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| 7/20/2014 | Huset's Speedway - Brandon, SD 410 Sprints - Winged: All Star Circuit of Champions Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks, 360 Sprints - Non-Winged | Results | | Greg Gunderson (Winged Outlaw) | 1st | - | - | 8th |
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| 7/23/2014 | Luverne Fairground - Luverne, MN Micro Sprint Car Racing Winged A-Class: Miniakota Micro Sprint Series Generic 1 | Results | | Greg Gunderson (Winged A-Class) | - | - | - | 21st | | Greg Gunderson (Generic 1) | - | - | - | 21st |
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| 7/24/2014 | Renegade Speedway - Canby, MN Micro Sprint Car Racing Winged A-Class: Miniakota Micro Sprint Series Generic 1 | Results | | Greg Gunderson (Winged A-Class) | - | - | - | - |
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| 7/27/2014 | Huset's Speedway - Brandon, SD Micro Sprint Car Racing 410 Sprints - Winged: All Star Circuit of Champions Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks, 360 Sprints - Non-Winged | Results | | Greg Gunderson (Winged Outlaw) | 8th (DNF) | - | 2nd | 11th |
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| 8/3/2014 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks | Results | | Greg Gunderson (Winged Outlaw) | 4th | - | - | 11th |
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| 8/9/2014 | Wilmot Raceway - Wilmot, WI Micro Sprint Car Racing Winged A-Class: Badger 600 Winged Micros Midgets, Winged Outlaw | Results | | Greg Gunderson (Winged A-Class) | - | - | - | - |
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| 8/10/2014 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, 410 Sprints - Winged, Hobby Stocks, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks | Results | | Greg Gunderson (Winged Outlaw) | 1st | - | - | 5th | | Greg Gunderson (Winged A-Class) | - | - | - | - |
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| 8/31/2014 | Huset's Speedway - Brandon, SD Micro Sprint Car Racing 360 Sprints - Winged, 410 Sprints - Winged, Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks | Results | | Greg Gunderson (Winged Outlaw) | 2nd | - | - | 7th |
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| 9/1/2014 | Huset's Speedway - Brandon, SD 360 Sprints - Winged: Minnesota Mafia Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks | Results | | Greg Gunderson (Winged Outlaw) | 2nd | - | - | 2nd |
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| 9/5/2014 | St. Croix Speedway - St. Croix Falls, WI 22nd Annual (Earl) Kouba Memorial Winged Outlaw: Minnesota Micro Sprints 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series 360 Sprints - Winged, DIRTcar Sport Compact, Factory Stocks, Stock Cars, Winged A-Class, Vintage Full Body Stock Cars, Vintage Modifieds | Results | | Greg Gunderson (Winged Outlaw) | 2nd | - | - | 1st | | Greg Gunderson (Winged A-Class) | - | - | - | - |
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| 9/7/2014 | Huset's Speedway - Brandon, SD 410 Sprints - Winged, Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks | Results | | Greg Gunderson (Winged Outlaw) | 3rd | - | - | 2nd |
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| 9/19/2014 | Interstate Speedway (SD) - Jefferson, SD Micro Sprint Car Racing Winged A-Class: Miniakota Micro Sprint Series Generic 1 | Results | | Greg Gunderson (Winged A-Class) | - | - | - | 2nd | | Greg Gunderson (Generic 1) | - | - | - | 2nd |
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| 9/26/2014 | Sweet Springs Motorsports Complex - Sweet Springs, MO Micro Sprint Car Racing Restricted 'A' Class, Winged A-Class | Results | | Greg Gunderson (Winged A-Class) | - | - | - | - |
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| 9/27/2014 | Sweet Springs Motorsports Complex - Sweet Springs, MO Micro Sprint Car Racing Restricted 'A' Class, Winged A-Class | Results | | Greg Gunderson (Winged A-Class) | - | - | - | - |
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| 10/8/2014 | Sweet Springs Motorsports Complex - Sweet Springs, MO Micro Sprint Car Racing Winged A-Class | Results | | Greg Gunderson (Winged A-Class) | - | - | - | - |
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| 10/9/2014 | Sweet Springs Motorsports Complex - Sweet Springs, MO Micro Sprint Car Racing Restricted 'A' Class, Winged A-Class | Results | | Greg Gunderson (Winged A-Class) | - | - | - | - |
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| 10/10/2014 | Sweet Springs Motorsports Complex - Sweet Springs, MO Micro Sprint Car Racing Restricted 'A' Class, Winged A-Class | Results | | Greg Gunderson (Winged A-Class) | - | - | - | - |
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| 10/11/2014 | Sweet Springs Motorsports Complex - Sweet Springs, MO Micro Sprint Car Racing Restricted 'A' Class, Winged A-Class | Results | | Greg Gunderson (Winged A-Class) | - | - | - | - |
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