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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 | | Brian Ross (Winged Outlaw) | - | - | - | - | | Brian Ross (Non-Wing Outlaw) | 7th | - | - | - | | Brian Ross (Winged A-Class) | - | - | - | - |
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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 | | Brian Ross (Winged Outlaw) | 9th | - | - | - | | Brian Ross (Non-Wing Outlaw) | - | - | - | - | | Brian Ross (Winged A-Class) | 9th | - | - | - |
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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 | | Brian Ross (Winged Outlaw) | - | - | - | - | | Brian Ross (Non-Wing Outlaw) | - | - | - | - | | Brian Ross (Winged A-Class) | - | - | - | - |
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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 | | Brian Ross (Winged Outlaw) | - | - | - | - | | Brian Ross (Non-Wing Outlaw) | - | - | - | - | | Brian Ross (Winged A-Class) | - | - | - | - |
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| 3/23/2019 | I-30 Speedway - Little Rock, AR 360 Sprints - Winged, Winged Outlaw | Results | | Brian Ross (Winged Outlaw) | - | - | - | 4th |
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| 3/29/2019 | I-30 Speedway - Little Rock, AR 360 Sprints - Winged: ASCS Sooner Region with ASCS Lone Star Region, ASCS Mid-South Region Winged Outlaw | Results | | Brian Ross (Winged Outlaw) | - | - | - | 8th |
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| 6/1/2019 | I-30 Speedway - Little Rock, AR | Results | | Brian Ross (Winged Outlaw) | - | - | - | 8th |
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| 6/29/2019 | I-30 Speedway - Little Rock, AR 305 Sprints - Winged: MSCA-Mid-South Sprint Car Association Winged Outlaw | Results | | Brian Ross (Winged Outlaw) | - | - | - | 7th |
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| 7/20/2019 | I-30 Speedway - Little Rock, AR | Results | | Brian Ross (Winged Outlaw) | - | - | - | 7th |
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| 7/27/2019 | I-30 Speedway - Little Rock, AR 360 Sprints - Winged: ASCS Mid-South Region Winged Outlaw | Results | | Brian Ross (Winged Outlaw) | - | - | - | 8th |
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| 8/23/2019 | Southern Illinois Raceway - Marion, IL Winged Outlaw, Winged A-Class | Results | | Brian Ross (Winged A-Class) | 10th | - | 10th | - |
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| 8/24/2019 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged A-Class | Results | | Brian Ross (Winged A-Class) | 9th | - | 10th | - |
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| 8/31/2019 | Riverside International Speedway - West Memphis, AR JIMMY HUFFMAN MEMORIAL 305 Sprints - Winged: MSCA-Mid-South Sprint Car Association Stock Cars, A Modifieds, Winged A-Class, Dirt Late Models | Results | | Brian Ross (Winged A-Class) | 5th | - | - | 6th |
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| 9/7/2019 | Riverside International Speedway - West Memphis, AR FALL NATIONALS 305 Sprints - Winged: MSCA-Mid-South Sprint Car Association 360 Sprints - Winged, Stock Cars, Winged A-Class, Dirt Late Models | Results | | Brian Ross (Winged A-Class) | 4th | - | - | 9th |
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| 9/21/2019 | Riverside International Speedway - West Memphis, AR GRASSROOTS SPECIAL 305 Sprints - Winged: MSCA-Mid-South Sprint Car Association Stock Cars, A Modifieds, Winged A-Class, Dirt Late Models | Results | | Brian Ross (Winged A-Class) | 3rd | - | - | 3rd |
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| 10/19/2019 | I-30 Speedway - Little Rock, AR Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw | Results | | Brian Ross (Winged Outlaw) | 5th | - | - | 13th |
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