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| 4/30/2021 | Coles County Speedway - Mattoon, IL Opening Night Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Larry Drake (Winged Outlaw) | DNS | - | - | - |
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| 5/1/2021 | Macon Speedway - Macon, IL CEFCU Kid's Club Regular Night of Racing DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Larry Drake (Winged A-Class) | 6th | - | - | 12th |
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| 5/7/2021 | Coles County Speedway - Mattoon, IL Weekly Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Larry Drake (Winged Outlaw) | 1st | - | - | 8th |
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| 5/15/2021 | Southern Illinois Raceway - Marion, IL Maier's Tidy Bowl Dwarf Special/Throwback Night Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Larry Drake (Winged Outlaw) | 5th | - | - | - |
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| 6/4/2021 | Coles County Speedway - Mattoon, IL Weekly Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Larry Drake (Winged Outlaw) | 1st | - | - | 1st |
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| 6/5/2021 | Southern Illinois Raceway - Marion, IL Performance Electronics Prelude to the Hustle Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Larry Drake (Winged Outlaw) | 1st | - | - | 8th |
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| 6/18/2021 | Southern Illinois Raceway - Marion, IL Engler Machine and Tool Highbanks Hustle Night 1 Winged A-Class | Results | | Larry Drake (Winged A-Class) | 3rd | - | 9th | - |
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| 6/19/2021 | Southern Illinois Raceway - Marion, IL Engler Machine and Tool Highbanks Hustle Final Winged A-Class | Results | | Larry Drake (Winged A-Class) | 1st | - | 1st | 15th |
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| 6/26/2021 | Southern Illinois Raceway - Marion, IL Points Night/HART Non-Wing Series Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Larry Drake (Winged Outlaw) | DNS | - | - | DNS |
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| 7/3/2021 | Wayne County Speedway - Wayne City, IL Season Opener Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Larry Drake (Winged Outlaw) | 2nd | - | - | 2nd |
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| 7/17/2021 | Southern Illinois Raceway - Marion, IL Ike Dealership JR Sprint Special/Rising Stars Night Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Larry Drake (Winged Outlaw) | 2nd | - | - | 3rd |
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| 7/23/2021 | Coles County Speedway - Mattoon, IL Non Wing Hart Series Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Larry Drake (Winged Outlaw) | - | - | - | - | | Larry Drake (Non-Wing Outlaw) | 5th | - | - | 11th |
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| 8/7/2021 | Wayne County Speedway - Wayne City, IL Hyper NON-Wing Outlaws $1250 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Larry Drake (Winged Outlaw) | 4th | - | - | 5th |
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| 8/27/2021 | Wayne County Speedway - Wayne City, IL Showdown in Beantown Night #1 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Larry Drake (Winged Outlaw) | 3rd | - | 1st | 19th |
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| 8/28/2021 | Wayne County Speedway - Wayne City, IL Showdown in Beantown Night #2 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Larry Drake (Winged Outlaw) | 7th (DNF) | - | DNS | - |
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| 9/11/2021 | Wayne County Speedway - Wayne City, IL Remembrance Weekend HART & MMSA Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints | Results | | Larry Drake (Winged Outlaw) | 2nd | - | - | DNS |
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| 9/18/2021 | Miami County Raceway - Peru, IN Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Hybrid 600cc Micros, Senior Micros | Results | | Larry Drake (Winged Outlaw) | 2nd | - | - | 1st |
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| 10/9/2021 | Southern Illinois Raceway - Marion, IL Open Race/Chase Make-up Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Larry Drake (Winged Outlaw) | 4th | - | - | 8th (DNF) |
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