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| 1/1/2016 | Tulsa Expo Raceway - Tulsa, OK Racing Midgets, Economy Midgets, Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, 410 Sprints - Non-Winged, Junior Sprints, 1200cc Outlaws Non-Winged Minis, 1200cc Outlaws Winged Minis | Results | | Harley Hollan (Winged Outlaw) | 3rd | - | - | - | | Harley Hollan (Winged A-Class) | - | - | - | - |
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| 1/2/2016 | Tulsa Expo Raceway - Tulsa, OK Racing Midgets, Economy Midgets, Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, 410 Sprints - Non-Winged, Junior Sprints, 1200cc Outlaws Non-Winged Minis, 1200cc Outlaws Winged Minis | Results | | Harley Hollan (Winged Outlaw) | - | - | - | 19th | | Harley Hollan (Winged A-Class) | - | - | 11th (DNF) | - |
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| 1/13/2016 | Tulsa Expo Raceway - Tulsa, OK Qualifying Night 2 Midgets | Results | | Harley Hollan (Midgets) | 5th | - | 11th | - |
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| 1/16/2016 | Tulsa Expo Raceway - Tulsa, OK Championship Night Midgets, Non-Wing Outlaw, Stock Non-Wing | Results | | Harley Hollan (Midgets) | - | - | - | - |
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| 4/8/2016 | Creek County Speedway - Sapulpa, OK ASCS Red River Region Sprint Cars "Light Up the Creek Blue" 360 Sprints - Winged: ASCS Red River Region Winged Outlaw: NOW600 Outlaw Micros Champ 360 Sprints - Non Winged | Results | | Harley Hollan (Winged Outlaw) | 6th | - | - | 12th |
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| 4/15/2016 | Belle-Clair Speedway - Belleville, IL Non-Winged Sprints: POWRi WAR Sprints Stock Cars, Winged Outlaw, Stock Non-Wing, 410 Sprints - Non-Winged, Vintage Full Body Stock Cars, Dwarf | Results | | Harley Hollan (Winged Outlaw) | 5th | - | 6th | - |
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| 5/21/2016 | Southern Illinois Raceway - Marion, IL Weekly Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Dwarf, 600cc Modifieds | Results | | Harley Hollan (Winged Outlaw) | - | - | - | 5th |
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| 6/17/2016 | Southern Illinois Raceway - Marion, IL High Banks Hustle IV - Night 1 Winged Outlaw | Results | | Harley Hollan (Winged Outlaw) | DNS | - | - | - |
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| 6/18/2016 | Southern Illinois Raceway - Marion, IL High Banks Hustle IV - Finale Winged Outlaw | Results | | Harley Hollan (Winged Outlaw) | DNS | - | - | - |
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| 7/7/2016 | Creek County Speedway - Sapulpa, OK Sooner Sweep Night 1 360 Sprints - Winged: ASCS Red River Region Winged Outlaw: NOW600 Outlaw Micros Champ 360 Sprints - Non Winged | Results | | Harley Hollan (Winged Outlaw) | 1st | - | - | 3rd |
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| 12/26/2016 | Tulsa Expo Raceway - Tulsa, OK Early Parking Economy Midgets, Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 1200cc Outlaws Non-Winged Minis, 1200cc Outlaws Winged Minis | Results | | Harley Hollan (Winged Outlaw) | - | - | - | - | | Harley Hollan (Non-Wing Outlaw) | - | - | - | - | | Harley Hollan (Stock Non-Wing) | - | - | - | - |
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| 12/28/2016 | Tulsa Expo Raceway - Tulsa, OK Practice / Races Winged Outlaw: Tulsa Shootout Economy Midgets, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 1200cc Outlaws Non-Winged Minis, 1200cc Outlaws Winged Minis | Results | | Harley Hollan (Winged Outlaw) | - | - | - | - | | Harley Hollan (Non-Wing Outlaw) | 2nd | - | - | - | | Harley Hollan (Stock Non-Wing) | - | - | - | - |
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| 12/29/2016 | Tulsa Expo Raceway - Tulsa, OK Races Winged Outlaw: Tulsa Shootout Economy Midgets, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 1200cc Outlaws Non-Winged Minis, 1200cc Outlaws Winged Minis | Results | | Harley Hollan (Winged Outlaw) | 1st | - | - | - | | Harley Hollan (Non-Wing Outlaw) | - | - | - | - | | Harley Hollan (Stock Non-Wing) | - | - | - | - |
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| 12/30/2016 | Tulsa Expo Raceway - Tulsa, OK Races Winged Outlaw: Tulsa Shootout Economy Midgets, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 1200cc Outlaws Non-Winged Minis, 1200cc Outlaws Winged Minis | Results | | Harley Hollan (Winged Outlaw) | - | - | - | - | | Harley Hollan (Non-Wing Outlaw) | - | - | - | - |
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| 12/31/2016 | Tulsa Expo Raceway - Tulsa, OK Races Winged Outlaw: Tulsa Shootout Economy Midgets, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 1200cc Outlaws Non-Winged Minis, 1200cc Outlaws Winged Minis | Results | | Harley Hollan (Winged Outlaw) | - | - | - | - | | Harley Hollan (Non-Wing Outlaw) | - | - | 1st | - |
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