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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 | | Harley Hollan (Winged Outlaw) | - | - | - | - | | Harley Hollan (Non-Wing Outlaw) | 5th | - | - | - | | Harley Hollan (Winged A-Class) | - | - | - | - | | Harley Hollan (600cc Modifieds) | - | - | - | - |
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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 | | Harley Hollan (Winged Outlaw) | 4th | - | - | - | | Harley Hollan (Non-Wing Outlaw) | - | - | - | - | | Harley Hollan (Winged A-Class) | 5th | - | - | - | | Harley Hollan (600cc Modifieds) | 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 | | Harley Hollan (Winged Outlaw) | - | 11th | - | - | | Harley Hollan (Non-Wing Outlaw) | - | - | - | - | | Harley Hollan (Winged A-Class) | - | 9th | - | - | | Harley Hollan (600cc Modifieds) | - | 4th | - | - |
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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 | | Harley Hollan (Winged Outlaw) | - | - | 5th | - | | Harley Hollan (Non-Wing Outlaw) | - | - | 3rd | - | | Harley Hollan (Winged A-Class) | - | - | 4th | - | | Harley Hollan (600cc Modifieds) | - | - | 1st | 20th |
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| 1/15/2019 | Tulsa Expo Raceway - Tulsa, OK Racing Night 2 Midgets: Chili Bowl Nationals | Results | | Harley Hollan (Midgets) | 8th (DNF) | - | - | - |
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| 1/19/2019 | Tulsa Expo Raceway - Tulsa, OK Racing Night 6 Midgets: Chili Bowl Nationals | Results | | Harley Hollan (Midgets) | - | - | - | - |
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| 3/21/2019 | Creek County Speedway - Sapulpa, OK 6th Annual Turnpike Challenge Midgets: POWRi National Midgets with POWRi West Midgets Winged Outlaw | Results | | Harley Hollan (Winged Outlaw) | 6th | - | - | 21st |
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| 3/22/2019 | I-44 Riverside Speedway - Oklahoma City, OK POWRi Lucas Oil National & West Midget League, POWRi Outlaws & A-Class Midgets: POWRi National Midgets with POWRi West Midgets Winged Outlaw, Winged A-Class | Results | | Harley Hollan (Winged Outlaw) | 3rd | - | - | 6th |
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| 3/23/2019 | I-44 Riverside Speedway - Oklahoma City, OK POWRi Lucas Oil National & West Midget League, POWRi Outlaws & Non-Wing Midgets: POWRi National Midgets with POWRi West Midgets Winged Outlaw, Stock Non-Wing | Results | | Harley Hollan (Winged Outlaw) | 5th | - | 5th | - |
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| 3/24/2019 | Port City Raceway - Tulsa, OK Turnpike Challenge - POWRi Lucas Oil National Midgets and POWRi Outlaw Micros Midgets: POWRi National Midgets with POWRi West Midgets Winged Outlaw | Results | | Harley Hollan (Winged Outlaw) | 1st | - | - | 7th |
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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 | | Harley Hollan (Winged Outlaw) | 1st | - | - | 14th |
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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 |
| 5/17/2019 | Belle-Clair Speedway - Belleville, IL Southern Illinois Shootout DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Factory Stock, DIRTcar Sport Compact, Winged Outlaw, B Modifieds | Results | | Harley Hollan (Winged Outlaw) | 5th | - | 1st | 5th |
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| 5/18/2019 | Southern Illinois Raceway - Marion, IL Southern Illinois Shootout Winged Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Harley Hollan (Winged Outlaw) | 4th | - | 4th | 12th |
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| 6/13/2019 | Brownstown Bullring - Brownstown, IL Illinois SPEED Week Midgets: POWRi National Midgets Winged Outlaw | Results | | Harley Hollan (Winged Outlaw) | 1st | - | - | 22nd |
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| 6/14/2019 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets Winged Outlaw | Results | | Harley Hollan (Winged Outlaw) | 4th | - | - | - |
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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 | | Harley Hollan (Winged Outlaw) | 2nd | - | - | 3rd |
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| 7/12/2019 | Valley Speedway - Grain Valley, MO Thunder In the Valley National Midgets by Rod End Supply Midgets: POWRi National Midgets with POWRi West Midgets Sprint Cars, Winged Outlaw | Results | | Harley Hollan (Winged Outlaw) | 2nd | - | - | 4th |
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| 7/13/2019 | Valley Speedway - Grain Valley, MO Thunder in the Valley National midgets by Rod End Supply Midgets: POWRi National Midgets with POWRi West Midgets Winged Outlaw | Results | | Harley Hollan (Winged Outlaw) | 3rd | - | - | 4th |
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| 8/23/2019 | Southern Illinois Raceway - Marion, IL Winged Outlaw, Winged A-Class | Results | | Harley Hollan (Winged A-Class) | 6th | - | 9th | - |
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| 8/24/2019 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged A-Class | Results | | Harley Hollan (Winged A-Class) | 2nd | - | 3rd | 13th |
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| 9/6/2019 | Jacksonville Speedway - Jacksonville, IL Herb Barlow Memorial 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi National Midgets Winged Outlaw | Results | | Harley Hollan (Winged Outlaw) | 3rd | - | - | 6th |
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| 9/13/2019 | Belle-Clair Speedway - Belleville, IL Midgets: POWRi Winged Outlaw | Results | | Harley Hollan (Winged Outlaw) | 2nd | - | - | 6th |
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| 9/14/2019 | Macon Speedway - Macon, IL Midgets: POWRi Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks | Results | | Harley Hollan (Winged Outlaw) | 1st | - | - | 2nd | | Harley Hollan (Winged A-Class) | - | - | - | 2nd |
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| 9/21/2019 | Port City Raceway - Tulsa, OK Weekly Show - POWRi West Midgets - 7PM Midgets: POWRi West Midgets Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Harley Hollan (Winged Outlaw) | 2nd | - | - | 4th |
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| 10/5/2019 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi National Midgets with POWRi 305 Sprints - Winged, Winged Outlaw | Results | | Harley Hollan (Winged Outlaw) | 8th | - | - | 7th |
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| 10/12/2019 | Southern Illinois Raceway - Marion, IL Southern Illinois Shootout Midgets: POWRi National Midgets Winged Outlaw | Results | | Harley Hollan (Winged Outlaw) | 3rd | - | - | 5th |
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| 10/13/2019 | Belle-Clair Speedway - Belleville, IL Midgets: POWRi Winged Outlaw, B Modifieds | Results | | Harley Hollan (Winged Outlaw) | 1st | - | - | 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 | | Harley Hollan (Winged Outlaw) | 1st | - | - | 2nd |
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