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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 | | Troy Leonard (Winged Outlaw) | 8th | - | - | DNS |
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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 | | Troy Leonard (Winged Outlaw) | 4th | - | - | - |
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| 6/29/2019 | 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 | | Troy Leonard (Winged Outlaw) | 2nd | - | - | - |
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| 7/13/2019 | 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 | | Troy Leonard (Winged Outlaw) | 2nd | - | - | - |
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| 7/19/2019 | Wayne County Speedway - Wayne City, IL Showdown in Bean Town Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints | Results | | Troy Leonard (Winged Outlaw) | 8th | - | 7th | - |
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| 7/20/2019 | Wayne County Speedway - Wayne City, IL Showdown in Bean Town Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints | Results | | Troy Leonard (Winged Outlaw) | 5th | - | 5th | - |
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| 8/3/2019 | 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 | | Troy Leonard (Winged Outlaw) | 4th | - | - | - |
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| 8/10/2019 | 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 | | Troy Leonard (Winged Outlaw) | 1st | - | - | - |
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| 8/31/2019 | Wayne County Speedway - Wayne City, IL HART Non-Wing/MMSA Labor Day Special Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Troy Leonard (Winged Outlaw) | 1st | - | - | 6th |
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| 9/7/2019 | Southern Illinois Raceway - Marion, IL Race/Chase night 1 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Troy Leonard (Sportsman Micros) | 3rd | - | - | 14th (DNF) |
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| 9/13/2019 | 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 | | Troy Leonard (Winged A-Class) | 3rd | - | - | - |
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| 9/14/2019 | Wayne County Speedway - Wayne City, IL Vintage Special Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints | Results | | Troy Leonard (Winged Outlaw) | 9th | - | - | 14th (DNF) | | Troy Leonard (Winged A-Class) | 2nd | - | - | 4th (DNF) |
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| 11/10/2019 | Wayne County Speedway - Wayne City, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, B Modifieds, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Troy Leonard (Winged A-Class) | 4th (DNF) | - | - | 3rd |
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