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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 | | Cole Roberts (Winged Outlaw) | - | - | - | - | | Cole Roberts (Winged A-Class) | - | - | - | - |
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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 | | Cole Roberts (Winged Outlaw) | 1st | - | - | - | | Cole Roberts (Winged A-Class) | 4th | - | - | - |
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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 | | Cole Roberts (Winged Outlaw) | - | - | - | - | | Cole Roberts (Winged A-Class) | - | 13th | - | - |
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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 | | Cole Roberts (Winged Outlaw) | - | 1st | - | 15th | | Cole Roberts (Winged A-Class) | - | - | 7th | - |
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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 | | Cole Roberts (Winged Outlaw) | 6th | - | 1st | 9th | | Cole Roberts (Winged A-Class) | 1st | - | - | 4th |
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| 5/22/2020 | Port City Raceway - Tulsa, OK T-Town Showdown - USAC Midgets Midgets: USAC National Midgets Winged A-Class, Stock Non-Wing | Results | | Cole Roberts (Stock Non-Wing) | 2nd | - | 2nd | 19th |
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| 5/23/2020 | Port City Raceway - Tulsa, OK T-Town Showdown - USAC Midgets Midgets: USAC National Midgets Stock Non-Wing | Results | | Cole Roberts (Stock Non-Wing) | 3rd | - | 2nd | 3rd |
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| 5/30/2020 | 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 | | Cole Roberts (Winged Outlaw) | 5th | - | - | 5th | | Cole Roberts (Winged A-Class) | 3rd | - | - | 2nd |
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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 | | Cole Roberts (Winged Outlaw) | 7th | - | 5th | - |
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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 | | Cole Roberts (Winged Outlaw) | 3rd | - | - | 5th | | Cole Roberts (Winged A-Class) | 5th | - | 4th | 11th |
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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 | | Cole Roberts (Winged Outlaw) | 3rd | - | - | 4th | | Cole Roberts (Winged A-Class) | 3rd | - | - | 3rd |
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| 6/20/2020 | 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 | | Cole Roberts (Winged Outlaw) | 5th | - | - | 4th | | Cole Roberts (Winged A-Class) | 6th | - | 3rd | 8th |
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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 | | Cole Roberts (Winged Outlaw) | 1st | - | - | 3rd | | Cole Roberts (Winged A-Class) | 2nd | - | - | 6th |
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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 | | Cole Roberts (Winged Outlaw) | - | 3rd | - | 4th | | Cole Roberts (Winged A-Class) | 2nd | - | - | 5th |
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| 7/11/2020 | 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 | | Cole Roberts (Winged Outlaw) | 4th | - | - | - | | Cole Roberts (Winged A-Class) | 1st | - | - | - |
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| 7/17/2020 | Port City Raceway - Tulsa, OK 2nd Annual PE3 & Engler Stock Nationals Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Sportsman Micros, Senior Micros | Results | | Cole Roberts (Winged A-Class) | 4th | - | - | 6th |
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| 7/18/2020 | Port City Raceway - Tulsa, OK 2nd Annual PE3 & Engler Stock Nationals Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Cole Roberts (Winged Outlaw) | 6th | - | - | 4th | | Cole Roberts (Winged A-Class) | 5th | - | 3rd | - |
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| 7/24/2020 | Southern Illinois Raceway - Marion, IL Engler Machine and Tool Highbanks Hustle Prelim Winged A-Class, Stock Non-Wing | Results | | Cole Roberts (Winged A-Class) | 6th | - | 5th | - |
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| 7/25/2020 | Southern Illinois Raceway - Marion, IL Engler Machine and Tool Highbanks Hustle Final Winged A-Class, Stock Non-Wing | Results | | Cole Roberts (Winged A-Class) | - | - | - | - |
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| 7/26/2020 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Rain Delay Winged A-Class | Results | | Cole Roberts (Winged A-Class) | 6th | - | - | - |
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| 8/1/2020 | 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 | | Cole Roberts (Winged Outlaw) | 5th | - | - | 5th | | Cole Roberts (Winged A-Class) | 4th | - | - | 5th |
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| 8/7/2020 | Port City Raceway - Tulsa, OK Non-Wing Nationals Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Cole Roberts (Winged Outlaw) | 6th | - | 6th | 12th | | Cole Roberts (Winged A-Class) | 7th | - | 5th | - |
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| 8/8/2020 | Port City Raceway - Tulsa, OK Non-Wing Nationals Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Cole Roberts (Winged Outlaw) | 2nd | - | - | 19th | | Cole Roberts (Winged A-Class) | 3rd | - | 1st | 11th |
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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 | | Cole Roberts (Winged Outlaw) | 3rd | - | - | 3rd | | Cole Roberts (Winged A-Class) | 4th | - | - | 9th |
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| 8/22/2020 | 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 | | Cole Roberts (Winged Outlaw) | 3rd | - | - | 2nd | | Cole Roberts (Winged A-Class) | 6th | - | 5th | 9th |
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| 8/29/2020 | 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 | | Cole Roberts (Winged Outlaw) | 3rd | - | - | 8th | | Cole Roberts (Winged A-Class) | 5th | - | 1st | 8th |
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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 | | Cole Roberts (Winged Outlaw) | 1st | - | - | 11th | | Cole Roberts (Winged A-Class) | 6th | - | 7th | - |
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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 | | Cole Roberts (Winged Outlaw) | 3rd | - | 7th | - | | Cole Roberts (Winged A-Class) | 2nd | - | 5th | - |
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| 9/12/2020 | Port City Raceway - Tulsa, OK Weekly Points Race - POWRi West Midgets Midgets: POWRi West Midgets with POWRi Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Cole Roberts (Winged Outlaw) | 4th | - | - | 3rd | | Cole Roberts (Winged A-Class) | 1st | - | - | 9th |
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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 | | Cole Roberts (Winged Outlaw) | 1st | - | - | 3rd | | Cole Roberts (Winged A-Class) | 2nd | - | - | 4th |
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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 | | Cole Roberts (Winged Outlaw) | 3rd | - | - | 2nd | | Cole Roberts (Winged A-Class) | 3rd | - | - | 7th |
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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 | | Cole Roberts (Winged Outlaw) | 4th | - | - | 8th | | Cole Roberts (Non-Wing Outlaw) | 3rd | - | - | 4th |
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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 | | Cole Roberts (Winged Outlaw) | 1st | - | - | 7th | | Cole Roberts (Non-Wing Outlaw) | 1st | - | - | 10th |
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