| | Heat | Dash | B Feature | A Feature |
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| 1/16/2019 | Tulsa Expo Raceway - Tulsa, OK Racing Night 3 Midgets: Chili Bowl Nationals | Results | | Tyler Robbins (Midgets) | DNS | - | - | - |
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| 1/19/2019 | Tulsa Expo Raceway - Tulsa, OK Racing Night 6 Midgets: Chili Bowl Nationals | Results | | Tyler Robbins (Midgets) | - | - | - | - |
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| 3/9/2019 | Southern Illinois Center - Duquoin, IL Midgets: USAC National Midgets Winged Outlaw | Results | | Tyler Robbins (Midgets) | 5th | - | 16th | - |
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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 | | Tyler Robbins (Midgets) | 6th | - | 7th | - |
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| 5/25/2019 | Wayne County Speedway - Wayne City, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Lightning Sprints | Results | | Tyler Robbins (Winged Outlaw) | 5th | - | - | 4th |
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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 | | Tyler Robbins (Winged Outlaw) | 2nd | - | - | 6th |
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| 6/1/2019 | Wayne County Speedway - Wayne City, IL USAC Regional Event/HART Non-Wing Micros Midgets, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints | Results | | Tyler Robbins (Midgets) | 5th | - | - | 8th | | Tyler Robbins (Non-Wing Outlaw) | 4th | - | - | 17th (DNF) |
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| 6/21/2019 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged A-Class | Results | | Tyler Robbins (Winged A-Class) | - | - | - | - |
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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 | | Tyler Robbins (Winged A-Class) | 3rd | - | - | 4th |
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| 7/6/2019 | Wayne County Speedway - Wayne City, IL Firecracker Classic Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Tyler Robbins (Winged Outlaw) | 2nd | - | - | 2nd |
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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 | | Tyler Robbins (Winged Outlaw) | 3rd | - | - | 7th |
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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 | | Tyler Robbins (Midgets) | 8th | - | - | 21st | | Tyler Robbins (Winged A-Class) | 3rd | - | - | 8th |
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| 8/2/2019 | Belle-Clair Speedway - Belleville, IL The Talker Guy 100 DIRTcar Late Models, DIRTcar Factory Stock, DIRTcar Sport Compact, Winged A-Class, B Modifieds | Results | | Tyler Robbins (Winged A-Class) | 6th | - | - | 4th |
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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 | | Tyler Robbins (Winged A-Class) | 7th | - | - | 3rd |
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| 8/24/2019 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged A-Class | Results | | Tyler Robbins (Winged A-Class) | 8th | - | 8th | - |
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| 9/6/2019 | Tri City Speedway - Granite City, IL Brad Yotter Memorial - UMP Late Models/UMP Mods/B-Mods/UMP Crate LM/Street Stock/Wing Micros DIRTcar Late Models, DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Tyler Robbins (Winged Outlaw) | 5th | - | - | 4th |
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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 | | Tyler Robbins (Non-Wing Outlaw) | 2nd | - | - | 9th |
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| 10/13/2019 | Belle-Clair Speedway - Belleville, IL Midgets: POWRi Winged Outlaw, B Modifieds | Results | | Tyler Robbins (Winged Outlaw) | 3rd | - | - | 16th |
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