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| 1/25/2019 | Hendry County Motorsports Park - Clewiston, FL Winter Heat 360 Sprints - Winged: USCS United Sprint Car Series Winged A-Class: Florida Mini Sprint Action Series | Results | | Tony Stewart (360 Sprints - Winged) | 2nd | - | - | 3rd |
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| 1/31/2019 | Ocala Speedway - Ocala, FL 410 Sprints - Winged: All Star Circuit of Champions Winged A-Class: Florida Mini Sprint Action Series Non-Wing Outlaw | Results | | Tony Stewart (410 Sprints - Winged) | 2nd | 1st | - | 3rd |
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| 2/1/2019 | Ocala Speedway - Ocala, FL 410 Sprints - Winged: All Star Circuit of Champions Winged A-Class: Florida Mini Sprint Action Series Non-Wing Outlaw | Results | | Tony Stewart (410 Sprints - Winged) | 3rd | - | - | 13th |
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| 2/2/2019 | Ocala Speedway - Ocala, FL 410 Sprints - Winged: All Star Circuit of Champions Winged A-Class: Florida Mini Sprint Action Series Non-Wing Outlaw | Results | | Tony Stewart (410 Sprints - Winged) | 1st | 1st | - | 1st |
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| 2/6/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds | Results | | Tony Stewart (410 Sprints - Winged) | 1st | 2nd | - | 13th |
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| 2/7/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds | Results | | Tony Stewart (410 Sprints - Winged) | 1st | 3rd | - | 7th |
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| 2/8/2019 | Ocala Speedway - Ocala, FL Winter Heat 360 Sprints - Winged: USCS United Sprint Car Series Midgets: USAC National Midgets | Results | | Tony Stewart (360 Sprints - Winged) | 1st | 2nd | - | 2nd |
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| 2/9/2019 | Ocala Speedway - Ocala, FL Winter Heat 360 Sprints - Winged: USCS United Sprint Car Series Midgets: USAC National Midgets | Results | | Tony Stewart (360 Sprints - Winged) | 1st | 2nd | - | 3rd |
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| 2/14/2019 | East Bay Raceway Park - Tampa, FL Winternationals Winged A-Class: Florida Mini Sprint Action Series 360 Sprints - Winged | Results | | Tony Stewart (360 Sprints - Winged) | - | - | - | 4th |
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| 2/15/2019 | East Bay Raceway Park - Tampa, FL Winternationals Winged A-Class: Florida Mini Sprint Action Series 360 Sprints - Winged | Results | | Tony Stewart (360 Sprints - Winged) | 1st | - | - | 2nd |
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| 2/22/2019 | Southern Raceway - Milton, FL Winter Heat Series - Battle at The Beach 360 Sprints - Winged: USCS United Sprint Car Series Vintage Full Body Stock Cars, Hornets, CRUSA Street Stocks | Results | | Tony Stewart (360 Sprints - Winged) | 2nd | - | - | 1st |
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| 2/23/2019 | Southern Raceway - Milton, FL Winter Heat Series - Battle at The Beach 360 Sprints - Winged: USCS United Sprint Car Series DIRTcar UMP Modifieds, Vintage Full Body Stock Cars, CRUSA Street Stocks, Pure Stock | Results | | Tony Stewart (360 Sprints - Winged) | 1st | - | - | 2nd |
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| 3/8/2019 | Chatam Raceway - Chatam, LA Winter Heat - Bayou Sprint Car Nationals 360 Sprints - Winged: USCS United Sprint Car Series | Results | | Tony Stewart (360 Sprints - Winged) | 1st | 1st | - | 2nd |
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| 3/9/2019 | Chatam Raceway - Chatam, LA Winter Heat - Bayou Sprint Car Nationals 360 Sprints - Winged: USCS United Sprint Car Series | Results | | Tony Stewart (360 Sprints - Winged) | 2nd | 4th | - | 3rd |
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| 3/16/2019 | Hattiesburg Speedway - Hattiesburg, MS Winter Heat 360 Sprints - Winged: United Sprint Car Series (Mid-South) | Results | | Tony Stewart (360 Sprints - Winged) | 1st | 4th | - | 2nd |
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| 4/6/2019 | Port Royal Speedway - Port Royal, PA 305 Sprints - Winged: PASS-Pa Sprint Series 305 with IMCA RaceSaver Sprints 410 Sprints - Winged | Results | | Tony Stewart (410 Sprints - Winged) | 2nd | - | - | 13th |
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| 4/11/2019 | Virginia Motor Speedway - Jamaica, VA 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds: Dirt Cup Challenge | Results | | Tony Stewart (410 Sprints - Winged) | 2nd | 6th | - | 6th |
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| 4/27/2019 | Smokey Harris Speedway - Haleburg, AL 360 Sprints - Winged: USCS United Sprint Car Series | Results | | Tony Stewart (360 Sprints - Winged) | 1st | - | - | 1st |
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| 5/4/2019 | Sharon Speedway - Hartford, OH 410 Sprints - Winged: All Star Circuit of Champions | Rain Out |
| 5/10/2019 | I-96 Speedway - Lake Odessa, MI Great Lakes Super Sprints 360 Sprints - Winged: (Formerly) Great Lakes Sprint Series B Modifieds, Street Stocks, Hornets, Mini Wedge, Mini Outlaws | Results | | Tony Stewart (360 Sprints - Winged) | 2nd | - | - | 1st |
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| 5/17/2019 | Attica Raceway Park - Attica, OH AFCS Sprints Eric Phillips 31st Anniversary Classic 410 Sprints - Winged, 305 Sprints - Winged | Results | | Tony Stewart (410 Sprints - Winged) | 2nd | - | - | 8th |
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| 5/18/2019 | Atomic Speedway - Chillicothe, OH Kids Night 410 Sprints - Winged: OVSCA-Ohio Valley Sprint Car Association Dirt Super Late Models, DIRTcar UMP Modifieds, Limited Sport Mod | Results | | Tony Stewart (410 Sprints - Winged) | 1st | - | - | 1st |
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| 5/24/2019 | Greenville Speedway - Greenville, MS USCS Speedweek Round 1 360 Sprints - Winged: USCS United Sprint Car Series | Results | | Tony Stewart (360 Sprints - Winged) | 1st | 1st | - | 12th |
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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 | | Tony Stewart (360 Sprints - Winged) | 2nd | - | 2nd | 21st |
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| 5/31/2019 | Nashville Fairgrounds Speedway - Nashville, TN Music City Outlaw Nationals 410 Sprints - Winged: World of Outlaws | Results | | Tony Stewart (410 Sprints - Winged) | 4th | - | - | 13th |
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| 6/1/2019 | Nashville Fairgrounds Speedway - Nashville, TN Music City Outlaw Nationals 410 Sprints - Winged: World of Outlaws | Results | | Tony Stewart (410 Sprints - Winged) | 1st | 5th | - | 4th |
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| 6/7/2019 | Outlaw Speedway - Dundee, NY 410 Sprints - Winged: All Star Circuit of Champions | Results | | Tony Stewart (410 Sprints - Winged) | 6th | - | - | 22nd |
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| 6/8/2019 | Stateline Speedway - Busti, NY 410 Sprints - Winged: All Star Circuit of Champions | Results | | Tony Stewart (410 Sprints - Winged) | 3rd | 3rd | - | 3rd |
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| 6/9/2019 | Weedsport Speedway - Weedsport, NY 410 Sprints - Winged: All Star Circuit of Champions | Results | | Tony Stewart (410 Sprints - Winged) | 4th | - | - | 8th |
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| 6/14/2019 | Attica Raceway Park - Attica, OH Ohio Speedweek Night #1 410 Sprints - Winged: All Star Circuit of Champions | Results | | Tony Stewart (410 Sprints - Winged) | 1st | 2nd | - | 26th |
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| 6/16/2019 | Muskingum County Speedway - Dresden, OH Ohio Speedweek Night #3 410 Sprints - Winged: All Star Circuit of Champions | Results | | Tony Stewart (410 Sprints - Winged) | 1st | 3rd | - | 24th |
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| 6/21/2019 | Atomic Speedway - Chillicothe, OH 410 Sprints - Winged: All Star Circuit of Champions | Canceled |
| 6/22/2019 | Wayne County Speedway - Orrville, OH Ohio Speedweek Night #9 410 Sprints - Winged: All Star Circuit of Champions | Results | | Tony Stewart (410 Sprints - Winged) | 5th | - | 15th (DNF) | - |
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| 7/12/2019 | Utica-Rome Speedway - Vernon, NY 410 Sprints - Winged: All Star Circuit of Champions | Results | | Tony Stewart (410 Sprints - Winged) | 3rd | 1st | - | 2nd |
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| 7/13/2019 | Orange County Fair Speedway - Middletown, NY 410 Sprints - Winged: All Star Circuit of Champions | Results | | Tony Stewart (410 Sprints - Winged) | 3rd | 6th | - | 3rd |
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| 7/14/2019 | Lebanon Valley Speedway - West Lebanon, NY 410 Sprints - Winged: All Star Circuit of Champions | Results | | Tony Stewart (410 Sprints - Winged) | 3rd | 7th | - | 6th |
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| 7/22/2019 | Ohsweken Speedway - Ohsweken, ON Burger Barn & Bradshaw Bros. presents Summer Nationals w/Tony Stewart, Christopher Bell & Rico Abreu 360 Sprints - Winged: PST-Patriot Sprint Tour Asphalt Mini Stocks | Results | | Tony Stewart (360 Sprints - Winged) | 4th | - | - | 4th |
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| 7/22/2019 | Oshweken Speedway - Oshweken, ON Northern Summer Nationals 360 Sprints - Winged | Results | | Tony Stewart (360 Sprints - Winged) | 4th | - | - | 4th |
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| 7/23/2019 | Ohsweken Speedway - Ohsweken, ON Arrow Express & Nitro 54 presents Summer Nationals-Tony Stewart, Christopher Bell & Rico Abreu 360 Sprints - Winged: PST-Patriot Sprint Tour Winged Crate Sprints: Action Sprint Tour Street Stocks, Dirt 4 cyl Modifieds | Results | | Tony Stewart (360 Sprints - Winged) | 3rd | - | - | 23rd |
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| 7/23/2019 | Oshweken Speedway - Oshweken, ON Northern Summer Nationals 360 Sprints - Winged | Results | | Tony Stewart (360 Sprints - Winged) | 3rd | - | - | 23rd |
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| 7/26/2019 | Jackson Motorplex - Jackson, MN Tony Stewart Night Presented by C&B Operations 410 Sprints - Winged: All Star Circuit of Champions 305 Sprints - Winged | Results | | Tony Stewart (410 Sprints - Winged) | 6th | - | 1st | 25th |
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| 7/27/2019 | Knoxville Raceway - Knoxville, IA 410 Sprints - Winged: All Star Circuit of Champions 360 Sprints - Winged, 305 Sprints - Winged | Results | | Tony Stewart (410 Sprints - Winged) | 7th | - | 7th | - |
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| 7/28/2019 | 34 Raceway - West Burlington, IA 410 Sprints - Winged: All Star Circuit of Champions Stock Cars, 2WD Trucks | Results | | Tony Stewart (410 Sprints - Winged) | 2nd | 1st | - | 1st |
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| 8/16/2019 | I-96 Speedway - Lake Odessa, MI Tony Stewarts - Allstar Circuit Of Champions / Great Lakes Super Sprints 360 Sprints - Winged: GLSS-Great Lakes Super Sprints 410 Sprints - Winged: All Star Circuit of Champions | Results | | Tony Stewart (410 Sprints - Winged) | 9th | - | 1st | 18th |
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| 8/17/2019 | Plymouth Speedway - Plymouth, IN $5,000 to win 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds, Street Stocks | Results | | Tony Stewart (410 Sprints - Winged) | 4th | - | - | 6th |
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| 8/22/2019 | Grandview Speedway - Bechtelsville, PA $5,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Tony Stewart (410 Sprints - Winged) | 5th | - | - | 8th |
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| 8/23/2019 | Williams Grove Speedway - Mechanicsburg, PA Twin 20s $4,000 to win X2 410 Sprints - Winged: All Star Circuit of Champions | Results | | Tony Stewart (410 Sprints - Winged) | 8th | - | 5th | - |
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| 8/25/2019 | BAPS Motor Speedway - York Haven, PA Justin Snyder Salute to the Troops $5,000 to win 410 Sprints - Winged: All Star Circuit of Champions 305 Sprints - Winged: PASS-Pa Sprint Series 305 | Results | | Tony Stewart (410 Sprints - Winged) | 4th | - | - | 11th |
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| 8/30/2019 | Wilmot Raceway - Wilmot, WI 410 Sprints - Winged: IRA Interstate Racing Association Non Wing Crate Sprints: Wisconsin wingLESS Sprints Lightning Sprints | Results | | Tony Stewart (410 Sprints - Winged) | 1st | - | - | 11th |
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| 8/31/2019 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI Sheboygan County Fair Race 360 Sprints - Winged: Midwest Sprint Car Association 410 Sprints - Winged: IRA Interstate Racing Association | Results | | Tony Stewart (410 Sprints - Winged) | 2nd | - | - | 1st |
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| 9/6/2019 | Port Royal Speedway - Port Royal, PA Night Before the 50 $5,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Tony Stewart (410 Sprints - Winged) | 1st | 2nd | - | 12th |
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| 9/7/2019 | Port Royal Speedway - Port Royal, PA 52nd Annual Tuscarora 50 $52,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Tony Stewart (410 Sprints - Winged) | 4th | - | 5th | 22nd |
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| 9/12/2019 | Atomic Speedway - Chillicothe, OH $5,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Tony Stewart (410 Sprints - Winged) | 1st | 5th | - | 8th |
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| 9/28/2019 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI WI State Sprint Championships 360 Sprints - Winged: Midwest Sprint Car Association 410 Sprints - Winged: IRA Interstate Racing Association Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Tony Stewart (410 Sprints - Winged) | 3rd | - | - | 22nd (DNF) |
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| 10/18/2019 | Super Bee Speedway - Chatham, LA 26th Annual Spooky 50 360 Sprints - Winged: USCS United Sprint Car Series Dirt Super Late Models, Factory Stocks, Hobby Stocks, B Modifieds, Street Stocks, Limited Sport Mod, Sport Compact | Results | | Tony Stewart (360 Sprints - Winged) | 1st | - | - | 1st |
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| 10/19/2019 | Super Bee Speedway - Chatham, LA 26th Annual Spooky 50 360 Sprints - Winged: USCS United Sprint Car Series Dirt Super Late Models, Factory Stocks, Hobby Stocks, B Modifieds, Street Stocks, Limited Sport Mod, Sport Compact | Results | | Tony Stewart (360 Sprints - Winged) | 1st | 3rd | - | 2nd |
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| 10/31/2019 | Texas Motor Speedway - Fort Worth, TX 360 Sprints - Winged: ASCS National with ASCS Lone Star Region | Results | | Tony Stewart (360 Sprints - Winged) | 4th | - | DNS | - |
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| 11/1/2019 | Texas Motor Speedway - Fort Worth, TX 360 Sprints - Winged: ASCS National with ASCS Lone Star Region | Results | | Tony Stewart (360 Sprints - Winged) | 3rd | - | - | 3rd |
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