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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 | | Dylan Pendergrass (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 | | Dylan Pendergrass (Winged A-Class) | 8th | - | - | - |
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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 | | Dylan Pendergrass (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 | | Dylan Pendergrass (Winged A-Class) | - | - | - | - |
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| 4/20/2019 | I-44 Riverside Speedway - Oklahoma City, OK 6th Annual Blue Blast for Autism Awareness Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Dylan Pendergrass (Winged A-Class) | 3rd | - | - | 7th | | Dylan Pendergrass (Stock Non-Wing) | 4th | - | - | 10th |
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| 5/4/2019 | I-44 Riverside Speedway - Oklahoma City, OK Weekly Points Race Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Dylan Pendergrass (Winged A-Class) | 5th | - | - | 6th |
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| 7/5/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship Winged Outlaw | Results | | Dylan Pendergrass (Winged Outlaw) | 6th | - | 14th (DNF) | - |
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| 7/6/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship Winged Outlaw | Results | | Dylan Pendergrass (Winged Outlaw) | DNS | - | 13th | - |
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| 7/13/2019 | I-44 Riverside Speedway - Oklahoma City, OK 7th Annual Going Green for cancer Awareness Weekly Points Race Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Dylan Pendergrass (Winged A-Class) | 3rd | - | - | DNS | | Dylan Pendergrass (Stock Non-Wing) | 7th (DNF) | - | - | 19th |
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| 10/26/2019 | Red Dirt Raceway - Meeker, OK KART Racing - Kart Track .... Red Dirt Kart CHAMPIONSHIP Junior Class, Junior Champ, Junior 1 Medium Dirt Karts, Junior 1 Heavy Dirt Karts, Junior 2 Animal Dirt Karts, Flat Adult Clone, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw, Clone Heavy Dirt Karts, Clone Medium Dirt Karts, Clone Lite Dirt Karts, Clone Super Heavy Dirt Karts, Flat Jr. 1 Clone Heavy, Flat Jr. 2 Clone Heavy, Flat Jr. 1 Clone | Results | | Dylan Pendergrass (500 Winged Open Outlaw) | 1st | - | - | 4th (DNF) |
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