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| 4/20/2019 | Macon Speedway - Macon, IL Dollar Dog / $2.00 Beer Night & Spectator Drags DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Dustin Clary (Winged A-Class) | 5th | - | - | 14th (DNF) |
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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 | | Dustin Clary (Winged Outlaw) | 8th | - | 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 | | Dustin Clary (Winged Outlaw) | 5th | - | 16th | - |
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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 | | Dustin Clary (Winged Outlaw) | 5th | - | - | - |
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| 5/25/2019 | Southern Illinois Raceway - Marion, IL Race/Armed Forces Night/Restrictor Special Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Dustin Clary (Winged Outlaw) | 6th | - | - | 9th | | Dustin Clary (600cc Modifieds) | - | - | - | - |
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| 5/31/2019 | Belle-Clair Speedway - Belleville, IL Lucas OIl MLRA Late Models Dirt Super Late Models: Lucas Oil MLRA DIRTcar Late Models, DIRTcar Factory Stock, DIRTcar Sport Compact, Winged Outlaw, B Modifieds | Results | | Dustin Clary (Winged Outlaw) | 3rd | - | - | 5th |
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| 6/1/2019 | Southern Illinois Raceway - Marion, IL Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Dustin Clary (Winged Outlaw) | 4th | - | - | 21st (DNF) |
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| 6/14/2019 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets Winged Outlaw | Results | | Dustin Clary (Winged Outlaw) | 2nd | - | - | - |
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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 | | Dustin Clary (Winged Outlaw) | 8th (DNF) | - | - | 16th |
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| 6/28/2019 | Belle-Clair Speedway - Belleville, IL DIRTcar UMP Modifieds, DIRTcar Sportsmans, DIRTcar Factory Stock, DIRTcar Sport Compact, Winged A-Class, B Modifieds | Results | | Dustin Clary (Winged A-Class) | 7th | - | 1st | 13th |
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| 7/13/2019 | Southern Illinois Raceway - Marion, IL Race/Gage Besing Memorial Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Dustin Clary (Winged Outlaw) | 2nd | - | - | 4th |
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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 | | Dustin Clary (Winged Outlaw) | 1st | - | - | 8th |
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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 | | Dustin Clary (Winged Outlaw) | 2nd | - | - | 10th |
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| 7/26/2019 | Belle-Clair Speedway - Belleville, IL Border WARS Midgets: POWRi National Midgets with POWRi Non-Winged Sprints: POWRi WAR Sprints Winged A-Class, B Modifieds | Results | | Dustin Clary (Winged A-Class) | 8th | - | 1st | 15th |
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| 8/10/2019 | Southern Illinois Raceway - Marion, IL Race/Dwarf special Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Dustin Clary (Winged Outlaw) | 1st | - | - | 3rd |
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| 8/23/2019 | Belle-Clair Speedway - Belleville, IL Big Ten Series DIRTcar Late Models, DIRTcar UMP Modifieds, Winged A-Class, B Modifieds | Results | | Dustin Clary (Winged A-Class) | 1st | - | - | 2nd |
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| 9/13/2019 | Belle-Clair Speedway - Belleville, IL Midgets: POWRi Winged Outlaw | Results | | Dustin Clary (Winged Outlaw) | 2nd | - | - | 8th |
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| 9/20/2019 | Tri City Speedway - Granite City, IL Season Championship - UMP Late Models/UMP Modifieds/B-Modifieds/UMP Crate LM/UMP St. Stocks/Micros DIRTcar Late Models, DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Dustin Clary (Winged Outlaw) | 5th | - | - | 5th |
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| 9/21/2019 | Southern Illinois Raceway - Marion, IL Race/Chase night 3 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Dustin Clary (Winged Outlaw) | 5th | - | - | 6th |
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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 | | Dustin Clary (Winged Outlaw) | 7th | - | - | 8th | | Dustin Clary (Non-Wing Outlaw) | 7th (DNF) | - | - | 9th |
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| 9/28/2019 | Southern Illinois Raceway - Marion, IL Race/Chase night 4 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Dustin Clary (Winged Outlaw) | 1st | - | - | 2nd |
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| 10/4/2019 | Wayne County Speedway - Wayne City, IL Fall Non-Wing Brawl Featuring HART Non-Wing Micros Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Dustin Clary (Non-Wing Outlaw) | 5th | - | 5th | - |
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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 | | Dustin Clary (Winged Outlaw) | 3rd | - | - | 4th | | Dustin Clary (Non-Wing Outlaw) | 6th (DNF) | - | 5th (DNF) | - |
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