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| 1/18/2019 | Tulsa Expo Raceway - Tulsa, OK Racing Night 5 Midgets: Chili Bowl Nationals | Results | | Tim Crawley (Midgets) | 2nd | 7th | 10th | - |
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| 1/19/2019 | Tulsa Expo Raceway - Tulsa, OK Racing Night 6 Midgets: Chili Bowl Nationals | Results | | Tim Crawley (Midgets) | - | - | - | - |
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| 3/9/2019 | Southern Illinois Center - DuQuoin, IL Midgets: USAC National Midgets Winged Outlaw | Results | | Tim Crawley (Midgets) | 5th | - | - | - |
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| 3/29/2019 | I-30 Speedway - Little Rock, AR 360 Sprints - Winged: ASCS Sooner Region with ASCS Lone Star Region, ASCS Mid-South Region Winged Outlaw | Results | | Tim Crawley (360 Sprints - Winged) | 3rd | - | - | 11th |
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| 4/19/2019 | Humboldt Speedway - Humboldt, KS ASCS Sooner vs. NCRA Sprint Cars Shootout 360 Sprints - Winged: ASCS Sooner Region Champ 360 Sprints - Winged, Factory Stocks, Midwest Modifieds, B Modifieds, Sport Compact | Results | | Tim Crawley (360 Sprints - Winged) | 1st | - | - | 7th | | Tim Crawley (Champ 360 Sprints - Winged) | - | - | - | - |
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| 4/20/2019 | Tri-State Speedway - Pocola, OK 360 Sprints - Winged: ASCS Sooner Region with ASCS Mid-South Region Street Stocks, Pure Stock, USRA B-Mods, USRA Modifieds | Results | | Tim Crawley (360 Sprints - Winged) | 1st | - | - | 3rd |
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| 4/27/2019 | Jackson Motor Speedway - Byram, MS 360 Sprints - Winged: ASCS Gulf South Region with ASCS Mid-South Region | Results | | Tim Crawley (360 Sprints - Winged) | 1st | - | - | 3rd |
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| 5/11/2019 | Monarch Motor Speedway - Wichita Falls, TX Sprint Cars 360 Sprints - Winged: NCRA-Sprint Car Bandits Champ 360 Sprints - Winged, Limited Sport Mod | Results | | Tim Crawley (360 Sprints - Winged) | - | - | - | 3rd |
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| 5/24/2019 | Greenville Speedway - Greenville, MS USCS Speedweek Round 1 360 Sprints - Winged: USCS United Sprint Car Series | Results | | Tim Crawley (360 Sprints - Winged) | 1st | - | - | 6th |
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| 5/25/2019 | Riverside International Speedway - West Memphis, AR USCS Speedweek Round 2 360 Sprints - Winged: USCS United Sprint Car Series 305 Sprints - Winged, Stock Cars, Dirt Late Models | Results | | Tim Crawley (360 Sprints - Winged) | 4th | 5th | - | 7th |
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| 6/14/2019 | Riverside International Speedway - West Memphis, AR Rescheduled Hooker Hood Classic 360 Sprints - Winged, 305 Sprints - Winged, Stock Cars, Dirt Late Models | Results | | Tim Crawley (360 Sprints - Winged) | 2nd | - | - | 16th |
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| 6/15/2019 | Riverside International Speedway - West Memphis, AR Greg Hodnett Memorial 305 Sprints - Winged: MSCA-Mid-South Sprint Car Association 360 Sprints - Winged, Stock Cars, Dirt Late Models | Results | | Tim Crawley (360 Sprints - Winged) | 4th | - | - | 6th |
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| 6/22/2019 | I-30 Speedway - Little Rock, AR 360 Sprints - Winged: ASCS Mid-South Region | Results | | Tim Crawley (360 Sprints - Winged) | 2nd | - | - | 4th |
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| 7/19/2019 | Crowleys Ridge Raceway - Paragould, AR 360 Sprints - Winged: ASCS Mid-South Region Factory Stocks, Winged A-Class, Pony Stock | Results | | Tim Crawley (360 Sprints - Winged) | 4th | - | - | 16th |
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| 7/20/2019 | Riverside International Speedway - West Memphis, AR 360 Sprints - Winged: ASCS Mid-South Region 305 Sprints - Winged: MSCA-Mid-South Sprint Car Association Stock Cars, Dirt Late Models | Results | | Tim Crawley (360 Sprints - Winged) | 4th | - | - | 6th |
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| 7/26/2019 | Poplar Bluff Motorsports Park - Poplar Bluff, MO 360 Sprints - Winged: ASCS Mid-South Region A Modifieds | Results | | Tim Crawley (360 Sprints - Winged) | 2nd | - | - | 1st |
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| 7/27/2019 | I-30 Speedway - Little Rock, AR 360 Sprints - Winged: ASCS Mid-South Region Winged Outlaw | Results | | Tim Crawley (360 Sprints - Winged) | 1st | - | - | 2nd |
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| 8/10/2019 | Lexington 104 Speedway - Lexington, TN 360 Sprints - Winged: USCS United Sprint Car Series | Results | | Tim Crawley (360 Sprints - Winged) | 2nd | - | - | 2nd |
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| 8/31/2019 | Lake Ozark Speedway - Eldon, MO 360 Sprints - Winged: ASCS National with ASCS Warrior Region Midgets: POWRi National Midgets with POWRi West Midgets | Results | | Tim Crawley (360 Sprints - Winged) | 4th | - | 5th | - |
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| 9/1/2019 | Lake Ozark Speedway - Eldon, MO 360 Sprints - Winged: ASCS National with ASCS Warrior Region Midgets: POWRi National Midgets with POWRi West Midgets | Results | | Tim Crawley (360 Sprints - Winged) | 3rd | - | - | 22nd |
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| 9/7/2019 | Riverside International Speedway - West Memphis, AR FALL NATIONALS 305 Sprints - Winged: MSCA-Mid-South Sprint Car Association 360 Sprints - Winged, Stock Cars, Winged A-Class, Dirt Late Models | Results | | Tim Crawley (360 Sprints - Winged) | 1st | - | - | 1st |
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| 9/14/2019 | I-30 Speedway - Little Rock, AR 360 Sprints - Winged: ASCS Sooner Region with ASCS Mid-South Region Winged Outlaw | Results | | Tim Crawley (360 Sprints - Winged) | 1st | 5th | - | 1st |
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| 9/19/2019 | Lucas Oil Speedway - Wheatland, MO 360 Sprints - Winged: ASCS National with ASCS Warrior Region Non-Winged Sprints: POWRi WAR Sprints | Results | | Tim Crawley (360 Sprints - Winged) | 2nd | - | 10th | - |
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| 9/20/2019 | Lucas Oil Speedway - Wheatland, MO 360 Sprints - Winged: ASCS National with ASCS Warrior Region Non-Winged Sprints: POWRi WAR Sprints | Results | | Tim Crawley (360 Sprints - Winged) | 5th | - | - | 10th |
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| 9/21/2019 | Lucas Oil Speedway - Wheatland, MO 360 Sprints - Winged: ASCS National with ASCS Warrior Region Non-Winged Sprints: POWRi WAR Sprints | Results | | Tim Crawley (360 Sprints - Winged) | 3rd | - | 9th | - |
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| 9/28/2019 | Jackson Motor Speedway - Byram, MS 360 Sprints - Winged: ASCS Mid-South Region | Results | | Tim Crawley (360 Sprints - Winged) | 1st | - | - | 2nd |
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| 10/4/2019 | I-30 Speedway - Little Rock, AR 360 Sprints - Winged: ASCS Mid-South Region | Results | | Tim Crawley (360 Sprints - Winged) | 5th | - | 7th | - |
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| 10/5/2019 | I-30 Speedway - Little Rock, AR 360 Sprints - Winged: ASCS Mid-South Region | Results | | Tim Crawley (360 Sprints - Winged) | 4th | - | 17th | 14th |
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| 12/19/2019 | The Dome at America's Center - St. Louis, MO 4th annual Arizona Sport Shirts Gateway Dirt Nationals presented by O’Reilly Auto Parts Midgets, Dirt Super Late Models, A Modifieds | Results | | Tim Crawley (Midgets) | 7th | - | - | 12th |
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| 12/21/2019 | The Dome at America's Center - St. Louis, MO 4th annual Arizona Sport Shirts Gateway Dirt Nationals presented by O’Reilly Auto Parts Midgets, Dirt Super Late Models, A Modifieds | Results | | Tim Crawley (Midgets) | - | - | 10th (DNF) | - |
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