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| 5/4/2019 | Miami County Raceway - Peru, IN Points Race #1. $1000 to Win NW Outlaw! Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Connor Wolf (Non-Wing Outlaw) | 9th | - | 13th | - |
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| 5/17/2019 | US 24 Speedway - Logansport, IN May 17 Rain out make up. Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Senior Micros | Results | | Connor Wolf (Winged Outlaw) | 5th | - | - | 7th (DNF) |
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| 5/18/2019 | Miami County Raceway - Peru, IN World Championship Final Tune-Up! Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros | Results | | Connor Wolf (Non-Wing Outlaw) | 3rd | - | 2nd | 15th |
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| 5/23/2019 | Miami County Raceway - Peru, IN Performance Electronics Non-Wing World Championship Prelim Night #1 Non-Wing Outlaw | Results | | Connor Wolf (Non-Wing Outlaw) | 4th | - | 12th | - |
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| 5/24/2019 | Miami County Raceway - Peru, IN Performance Electronics Non-Wing World Championship Prelim Night #2 Non-Wing Outlaw | Results | | Connor Wolf (Non-Wing Outlaw) | 4th | - | 12th | - |
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| 5/25/2019 | Miami County Raceway - Peru, IN Performance Electronics Non-Wing World Championship Non-Wing Outlaw | Results | | Connor Wolf (Non-Wing Outlaw) | 6th | - | - | - |
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| 6/8/2019 | US 24 Speedway - Logansport, IN 2nd Point night A-Wing $500 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Connor Wolf (Winged Outlaw) | 4th | - | - | DNS |
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| 6/13/2019 | US 24 Speedway - Logansport, IN Performance Electronic NW Shootout Practice Non-Wing Outlaw | Results | | Connor Wolf (Non-Wing Outlaw) | - | - | - | - |
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| 6/14/2019 | US 24 Speedway - Logansport, IN Performance Electronic NW Shootout #THEBIGDANCE Preliminary night $1000 to win Non-Wing Outlaw, Restricted Non Winged Micros | Results | | Connor Wolf (Non-Wing Outlaw) | - | - | - | - |
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| 7/3/2019 | Miami County Raceway - Peru, IN Firecracker 40's. $1000 to Win Non-Wing Outlaw and Outlaw Wing Plus Huge Fireworks Show! Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Connor Wolf (Winged Outlaw) | 1st | - | - | 13th (DNF) |
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| 7/6/2019 | Miami County Raceway - Peru, IN Stock 600 Showdown. $600 to Win A-Class Winged! Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Connor Wolf (Winged Outlaw) | 7th | - | - | 2nd |
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| 7/27/2019 | US 24 Speedway - Logansport, IN Outlaw Wing $300 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Connor Wolf (Winged Outlaw) | 4th | - | - | 4th |
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| 8/3/2019 | US 24 Speedway - Logansport, IN 6th point race 2nd Annual Honoring Our Hero's Senior Class $500 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Restricted Non Winged Micros, Winged A-Class, Junior Sprints, Senior Micros | Results | | Connor Wolf (Winged Outlaw) | 1st | - | - | 7th |
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| 8/8/2019 | US 24 Speedway - Logansport, IN Triple XXX Root Beer Outlaw Wing #KINGOFTHEWING Practice Winged Outlaw, Winged A-Class | Results | | Connor Wolf (Winged Outlaw) | - | - | - | - |
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| 8/9/2019 | US 24 Speedway - Logansport, IN Triple XXX Root Beer Outlaw Wing #KINGOFTHEWING Preliminary night $1000 to win Winged Outlaw, Winged A-Class | Results | | Connor Wolf (Winged Outlaw) | 3rd | - | 11th | - |
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| 8/10/2019 | US 24 Speedway - Logansport, IN Triple XXX Root Beer Outlaw Wing #KINGOFTHEWING $8000 to win Winged Outlaw, Winged A-Class | Results | | Connor Wolf (Winged Outlaw) | 1st | - | - | - |
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| 8/24/2019 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged A-Class | Results | | Connor Wolf (Winged A-Class) | 8th | - | 12th | - |
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| 9/21/2019 | Miami County Raceway - Peru, IN Sam Davis Memorial + Senior Shuffle! $500 to Win Senior Class! (Jr, Rest, and A Racing NW) Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Connor Wolf (Winged Outlaw) | 3rd | - | - | 8th (DNF) |
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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 | | Connor Wolf (Winged Outlaw) | 1st | - | - | - | | Connor Wolf (Non-Wing Outlaw) | 2nd | - | - | - |
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| 10/5/2019 | Miami County Raceway - Peru, IN Elbows Up! Brad Joyce Memorial. $1000 to Win Outlaw NW! (Jr, Rest, and A Racing NW!) Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Connor Wolf (Winged Outlaw) | 3rd | - | - | - | | Connor Wolf (Non-Wing Outlaw) | 3rd | - | 2nd | 15th (DNF) |
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| 10/12/2019 | Southern Illinois Raceway - Marion, IL Southern Illinois Shootout Midgets: POWRi National Midgets Winged Outlaw | Results | | Connor Wolf (Winged Outlaw) | 4th | - | 2nd | 20th |
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