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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 | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 20th |
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| 2/8/2019 | Volusia Speedway Park - De Leon Springs, FL DirtCar Nationals 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 2nd | 20th |
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| 2/9/2019 | Volusia Speedway Park - De Leon Springs, FL DirtCar Nationals 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 9th |
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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 | | Jason Sides (360 Sprints - Winged) | - | - | 1st | 8th |
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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 | | Jason Sides (360 Sprints - Winged) | 2nd | - | - | 14th |
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| 2/16/2019 | East Bay Raceway Park - Tampa, FL Winternationals Winged A-Class: Florida Mini Sprint Action Series 360 Sprints - Winged | Results | | Jason Sides (360 Sprints - Winged) | - | - | - | 21st (DNF) |
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| 2/27/2019 | Dirt Track at Las Vegas - Las Vegas, NV 410 Sprints - Winged: World of Outlaws A Modifieds, 360 Sprints - Non-Winged | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 24th |
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| 2/28/2019 | Dirt Track at Las Vegas - Las Vegas, NV 410 Sprints - Winged: World of Outlaws Asphalt Late Models: NASCAR K&N Pro Series - West 360 Sprints - Non-Winged | Results | | Jason Sides (410 Sprints - Winged) | 1st | 2nd | - | 9th |
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| 3/9/2019 | Thunderbowl Raceway - Tulare, CA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 10th | - |
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| 3/15/2019 | Silver Dollar Speedway - Chico, CA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | - | - |
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| 4/6/2019 | Arizona Speedway - Queen Creek, AZ World of Outlaws 410 Sprints - Winged: World of Outlaws Non-Winged Sprints: San Tan Ford ASCS Desert Sprint Car Series | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | - | 16th |
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| 4/12/2019 | Devil's Bowl Speedway - Mesquite, TX Texas Outlaw Nationals 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 2nd | 16th |
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| 4/26/2019 | Lake Ozark Speedway - Eldon, MO WORLD OF OUTLAWS SPRINT CARS!!! + POWRI Racesavers, Midwest Lighting Sprints 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged, Lightning Sprints | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 17th |
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| 5/10/2019 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws 410 Sprints - Non-Winged: USAC National Sprint Cars | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | 5th | 20th | | Jason Sides (410 Sprints - Non-Winged) | - | - | - | - |
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| 5/25/2019 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 8th |
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| 5/31/2019 | Nashville Fairgrounds Speedway - Nashville, TN Music City Outlaw Nationals 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 6th | - |
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| 6/1/2019 | Nashville Fairgrounds Speedway - Nashville, TN Music City Outlaw Nationals 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 2nd | 6th | - | 11th |
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| 6/4/2019 | Fairbury Speedway - Fairbury, IL 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 21st |
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| 6/7/2019 | River Cities Speedway - Grand Forks, ND 410 Sprints - Winged: World of Outlaws WISSOTA Late Model | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | - | 17th |
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| 6/8/2019 | Granite City Motor Park - Sauk Rapids, MN 410 Sprints - Winged: World of Outlaws Winged A-Class, WISSOTA Super Stock | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 16th |
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| 6/27/2019 | Jackson Motorplex - Jackson, MN 41st annual AGCO Jackson Nationals 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 20th |
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| 6/28/2019 | Jackson Motorplex - Jackson, MN 41st annual AGCO Jackson Nationals 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 1st | 23rd |
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| 6/29/2019 | Jackson Motorplex - Jackson, MN 41st annual AGCO Jackson Nationals 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 19th |
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| 7/3/2019 | Brown County Speedway - Aberdeen, SD 410 Sprints - Winged: World of Outlaws Dirt Late Models: Tri-State Late Models Pure Stock | Results | | Jason Sides (410 Sprints - Winged) | 1st | 4th | - | 17th |
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| 7/17/2019 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws 410 Sprints - Non-Winged: USAC National Sprint Cars | Results | | Jason Sides (410 Sprints - Winged) | 10th | - | - | - |
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| 7/18/2019 | Eldora Speedway - Rossburg, OH Jokers Wild 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | - | - |
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| 7/19/2019 | Eldora Speedway - Rossburg, OH The Knight before the Kings Royal 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | - | - |
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| 7/20/2019 | Eldora Speedway - Rossburg, OH 36th Annual Kings Royal 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | 17th | - |
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| 7/23/2019 | Lernerville Speedway - Sarver, PA Silver Cup 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 23rd |
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| 8/2/2019 | Federated Auto Parts I-55 Raceway - Pevely, MO Iron Man 55 410 Sprints - Winged: World of Outlaws Midgets: POWRi National Midgets with POWRi West Midgets | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 2nd | 15th |
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| 8/3/2019 | Federated Auto Parts I-55 Raceway - Pevely, MO Iron Man 55 410 Sprints - Winged: World of Outlaws Midgets: POWRi National Midgets with POWRi West Midgets DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 2nd | 15th |
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| 8/8/2019 | Knoxville Raceway - Knoxville, IA Knoxville Nationals 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 1st | - | - | 12th |
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| 8/9/2019 | Knoxville Raceway - Knoxville, IA Knoxville Nationals 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | 19th | - |
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| 8/10/2019 | Knoxville Raceway - Knoxville, IA Knoxville Nationals 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | - | - | - | - |
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| 8/16/2019 | River Cities Speedway - Grand Forks, ND 410 Sprints - Winged: World of Outlaws WISSOTA Late Model | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 16th |
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| 8/23/2019 | Black Hills Speedway - Rapid City, SD 410 Sprints - Winged: World of Outlaws Hobby Stocks, WISSOTA Street Stock | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | 5th | 13th |
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| 8/24/2019 | Big Sky Speedway - Billings, MT 410 Sprints - Winged: World of Outlaws WISSOTA Street Stock | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 11th |
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| 8/30/2019 | Skagit Speedway - Burlington, WA WORLD OF OUTLAWS 410 Sprints - Winged: World of Outlaws Economy Midgets: Northwest Focus Midget Series | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | - | 16th |
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| 8/31/2019 | Skagit Speedway - Burlington, WA WORLD OF OUTLAWS 410 Sprints - Winged: World of Outlaws Economy Midgets: Northwest Focus Midget Series | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 16th |
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| 9/2/2019 | Grays Harbor Raceway - Elma, WA WORLD OF OUTLAWS - Presented by Lucky Eagle Casino & Hotel 410 Sprints - Winged: World of Outlaws Economy Midgets: Northwest Focus Midget Series | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 13th | 17th |
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| 9/4/2019 | Willamette Speedway - Lebanon, OR Invational - Non Points 410 Sprints - Winged: World of Outlaws Limited Sprints - Winged: ISCS-Interstate Sprint Car Series (Limited) | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 9th | 14th |
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| 9/11/2019 | Placerville Speedway - Placerville, CA 410 Sprints - Winged: World of Outlaws Midgets: USAC Western Midgets 410 Sprints - Non-Winged: USAC Western States | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 5th | 23rd |
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| 9/20/2019 | Dodge City Raceway Park - Dodge City, KS 410 Sprints - Winged: World of Outlaws B Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 16th |
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| 9/21/2019 | Dodge City Raceway Park - Dodge City, KS 410 Sprints - Winged: World of Outlaws B Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 14th |
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| 9/25/2019 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 5th | - |
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| 9/27/2019 | Eldora Speedway - Rossburg, OH BeFour the Crowns Showdown 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | DNS | - | - | - |
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| 9/28/2019 | Lernerville Speedway - Sarver, PA Commonwealth Clash 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged: Allegheny Sprint Tour | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 1st | 13th |
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| 10/4/2019 | Williams Grove Speedway - Mechanicsburg, PA National Open 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 13th | - |
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| 10/5/2019 | Williams Grove Speedway - Mechanicsburg, PA National Open 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | 17th | - |
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| 10/13/2019 | Tri-State Speedway - Haubstadt, IN 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 5th | 18th |
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| 10/19/2019 | Lake Ozark Speedway - Eldon, MO Jason Johnson Classic / World Of Outlaws ! Invades For 2nd Time In 2019! 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 1st | 1st | - | 6th |
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| 10/25/2019 | Port Royal Speedway - Port Royal, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 15th | - |
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| 11/8/2019 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 16th | - |
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| 11/9/2019 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 8th (DNF) | - | DNS | - |
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