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| 1/1/2020 | Tulsa Expo Raceway - Tulsa, OK Morning Practice / Evening Races Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Tom Calico (Winged Outlaw) | - | - | - | - |
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| 1/2/2020 | Tulsa Expo Raceway - Tulsa, OK Races Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Tom Calico (Winged Outlaw) | 9th | - | - | - |
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| 1/3/2020 | Tulsa Expo Raceway - Tulsa, OK Races Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Tom Calico (Winged Outlaw) | - | - | - | - |
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| 1/4/2020 | Tulsa Expo Raceway - Tulsa, OK #WintheDriller Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Tom Calico (Winged Outlaw) | - | - | - | - |
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| 5/16/2020 | Port City Raceway - Tulsa, OK Spring Fling - Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Tom Calico (Winged Outlaw) | 6th | - | - | DNS |
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| 5/31/2020 | Port City Raceway - Tulsa, OK Seventh Annual Turnpike Challenge (Port City Raceway) Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw | Results | | Tom Calico (Winged Outlaw) | 8th | - | 11th | - |
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| 6/6/2020 | Port City Raceway - Tulsa, OK Weekly Points Race Midgets: POWRi West Midgets with POWRi Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Tom Calico (Winged Outlaw) | 5th | - | - | 14th |
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| 6/13/2020 | Port City Raceway - Tulsa, OK Sooner 600 Week - Night 4 Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Winged Outlaw, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Tom Calico (Winged Outlaw) | 6th | - | 2nd | 15th |
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| 6/26/2020 | Port City Raceway - Tulsa, OK 9th Annual Donnie Ray Crawford Memorial Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Tom Calico (Winged Outlaw) | 9th | - | 11th | - |
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| 6/27/2020 | Port City Raceway - Tulsa, OK 9th Annual Donnie Ray Crawford Memorial Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Tom Calico (Winged Outlaw) | 9th | - | 12th | - |
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| 8/15/2020 | Port City Raceway - Tulsa, OK Weekly Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Tom Calico (Winged Outlaw) | 7th | - | - | 12th |
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| 9/4/2020 | Port City Raceway - Tulsa, OK Pete Frazier Memorial - Show Up Points Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Winged Outlaw, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Tom Calico (Winged Outlaw) | 6th | - | 14th | - |
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| 9/5/2020 | Port City Raceway - Tulsa, OK Pete Frazier Memorial - Show Up Points Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Winged Outlaw, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Tom Calico (Winged Outlaw) | 7th | - | 11th | - |
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| 9/19/2020 | Port City Raceway - Tulsa, OK Weekly Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Tom Calico (Winged Outlaw) | 6th | - | - | 17th |
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| 9/26/2020 | Port City Raceway - Tulsa, OK Weekly Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Tom Calico (Winged Outlaw) | 8th | - | - | 16th |
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| 10/2/2020 | Port City Raceway - Tulsa, OK RUJO Rumble Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Hybrid 600cc Micros, Senior Micros | Results | | Tom Calico (Winged Outlaw) | DNS | - | - | 16th |
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| 10/3/2020 | Port City Raceway - Tulsa, OK RUJO Rumble Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Hybrid 600cc Micros, Senior Micros | Results | | Tom Calico (Winged Outlaw) | 6th | - | - | 13th |
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