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| 1/2/2019 | Tulsa Expo Raceway - Tulsa, OK Practice/Heat Races Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Tom Curran (Winged Outlaw) | - | - | - | - | | Tom Curran (Non-Wing Outlaw) | 3rd | - | - | - | | Tom Curran (Winged A-Class) | - | - | - | - | | Tom Curran (Stock Non-Wing) | - | - | - | - |
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| 1/3/2019 | Tulsa Expo Raceway - Tulsa, OK Race Day Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Tom Curran (Winged Outlaw) | 3rd | - | - | - | | Tom Curran (Non-Wing Outlaw) | - | - | - | - | | Tom Curran (Winged A-Class) | 3rd | - | - | - | | Tom Curran (Stock Non-Wing) | 4th | - | - | - |
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| 1/4/2019 | Tulsa Expo Raceway - Tulsa, OK Race Day Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Tom Curran (Winged Outlaw) | - | 3rd | - | - | | Tom Curran (Non-Wing Outlaw) | - | 1st | - | - | | Tom Curran (Winged A-Class) | - | 13th | - | - | | Tom Curran (Stock Non-Wing) | - | 12th | - | - |
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| 1/5/2019 | Tulsa Expo Raceway - Tulsa, OK Shootout Finale - Golden Driller Day! Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Tom Curran (Winged Outlaw) | - | - | - | 21st | | Tom Curran (Non-Wing Outlaw) | - | - | - | 7th | | Tom Curran (Winged A-Class) | - | - | 13th | - | | Tom Curran (Stock Non-Wing) | - | - | 15th | - |
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| 5/10/2019 | Belle-Clair Speedway - Belleville, IL Midwest Season Opener Midgets: POWRi National Midgets with POWRi Winged Outlaw, B Modifieds | Results | | Tom Curran (Winged Outlaw) | 1st | - | - | 11th |
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| 5/11/2019 | Southern Illinois Raceway - Marion, IL Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Rain Out |
| 5/18/2019 | Southern Illinois Raceway - Marion, IL Southern Illinois Shootout Winged Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Tom Curran (Winged Outlaw) | 7th | - | - | - |
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| 6/1/2019 | Southern Illinois Raceway - Marion, IL Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Tom Curran (Winged Outlaw) | 8th | - | 4th | 24th (DNF) |
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| 6/15/2019 | Southern Illinois Raceway - Marion, IL Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Tom Curran (Winged Outlaw) | 7th | - | - | 12th |
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| 7/5/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship Winged Outlaw | Results | | Tom Curran (Winged Outlaw) | 2nd | - | 5th | - |
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| 7/6/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship Winged Outlaw | Results | | Tom Curran (Winged Outlaw) | 5th | - | 5th | - |
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| 8/23/2019 | Southern Illinois Raceway - Marion, IL Winged Outlaw, Winged A-Class | Results | | Tom Curran (Winged A-Class) | 9th | - | 10th (DNF) | - |
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| 8/24/2019 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged A-Class | Results | | Tom Curran (Winged A-Class) | 6th | - | 12th (DNF) | - |
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