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| 5/10/2019 | Coles County Speedway - Mattoon, IL Weekly Race Winged Outlaw: American Micro Sprint Association Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Larry Drake (Winged Outlaw) | 1st | 1st | - | - |
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| 5/14/2019 | Wayne County Speedway - Wayne City, IL To Tired to Wait Tuesday Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Larry Drake (Winged Outlaw) | 2nd | - | - | 8th |
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| 6/1/2019 | Coles County Speedway - Mattoon, IL Weekly Race Winged Outlaw: American Micro Sprint Association Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Larry Drake (Winged Outlaw) | 2nd | - | - | - |
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| 8/17/2019 | Southern Illinois Raceway - Marion, IL Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Larry Drake (Winged Outlaw) | 7th | - | - | 11th |
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| 8/24/2019 | Macon Speedway - Macon, IL Church Night Featuring Faster Pastor Race / Kids Racecar rides / CEFCU Kid's Club DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Larry Drake (Winged A-Class) | 5th | - | - | 9th |
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| 8/31/2019 | Coles County Speedway - Mattoon, IL Weekly Race Winged Outlaw: American Micro Sprint Association Economy Midgets, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Larry Drake (Winged Outlaw) | 3rd | - | - | - |
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| 9/7/2019 | Macon Speedway - Macon, IL Skeff Distributing Presents Taylorville Night with Spectator Drags / Hornet World Championship DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Larry Drake (Winged A-Class) | 2nd | - | - | 3rd |
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| 9/14/2019 | Southern Illinois Raceway - Marion, IL Race/Chase night 2/Jerry Holder Memorial Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Larry Drake (Winged Outlaw) | 3rd | - | - | 4th |
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| 9/27/2019 | Wayne County Speedway - Wayne City, IL Bean Day Bash Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Larry Drake (Winged Outlaw) | 2nd | - | - | 4th |
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| 9/28/2019 | Coles County Speedway - Mattoon, IL Weekly Race Winged Outlaw: American Micro Sprint Association Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Larry Drake (Winged Outlaw) | 2nd | - | - | - |
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| 10/5/2019 | Wayne County Speedway - Wayne City, IL Fall Non-Wing Brawl w/ HART Non-Wing Micros Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Larry Drake (Winged Outlaw) | 2nd | - | - | 5th |
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