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| 2/5/2020 | 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) | 7th | - | 14th (DNF) | - |
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| 2/7/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 12th | 25th (DNF) |
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| 2/8/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 8th | 18th |
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| 2/9/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 7th | 22nd |
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| 2/13/2020 | East Bay Raceway Park - Tampa, FL King of the 360's 360 Sprints - Winged | Results | | Jason Sides (360 Sprints - Winged) | 5th | 2nd | 5th | - |
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| 2/15/2020 | East Bay Raceway Park - Tampa, FL King of the 360's 360 Sprints - Winged | Results | | Jason Sides (360 Sprints - Winged) | 2nd | - | - | 11th |
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| 5/8/2020 | Knoxville Raceway - Knoxville, IA 1st Race back ...no fans Invitational Only 48 Drivers 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 7th | 21st |
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| 5/15/2020 | Jackson Motorplex - Jackson, MN Great Lakes Shootout presented by Harvey's Roofing & Tweeter Contracting - IRA Sprint Car Series 410 Sprints - Winged: IRA Interstate Racing Association 305 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 1st | 18th |
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| 5/16/2020 | Jackson Motorplex - Jackson, MN Great Lakes Shootout presented by Tweeter Contracting and Harvey's Five Star Roofing 410 Sprints - Winged: IRA Interstate Racing Association | Rain Out |
| 5/22/2020 | Federated Auto Parts I-55 Raceway - Pevely, MO 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 17th |
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| 5/23/2020 | Federated Auto Parts I-55 Raceway - Pevely, MO 410 Sprints - Winged: World of Outlaws with MOWA-Midwest Open Wheel Association DIRTcar UMP Modifieds, DIRTcar Sportsmans, DIRTcar Sport Compact, B Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 11th | 18th |
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| 5/29/2020 | Lake Ozark Speedway - Eldon, MO 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 17th |
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| 5/30/2020 | Lake Ozark Speedway - Eldon, MO 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 12th |
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| 6/5/2020 | Beaver Dam Raceway - Beaver Dam, WI 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 1st | 17th |
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| 6/6/2020 | Beaver Dam Raceway - Beaver Dam, WI 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 11th |
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| 6/12/2020 | Knoxville Raceway - Knoxville, IA Brownells Big Guns Bash 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 12th | - |
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| 6/13/2020 | Knoxville Raceway - Knoxville, IA Brownells Big Guns Bash 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 10th | - |
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| 6/19/2020 | Tri-State Speedway - Haubstadt, IN 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 21st |
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| 6/20/2020 | Tri-State Speedway - Haubstadt, IN 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 17th |
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| 6/25/2020 | Jackson Motorplex - Jackson, MN AGCO Jackson Nationals featuring the World of Outlaws 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | - |
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| 6/26/2020 | Jackson Motorplex - Jackson, MN AGCO Jackson Nationals featuring the World of Outlaws 410 Sprints - Winged: World of Outlaws Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Jason Sides (410 Sprints - Winged) | 2nd | 1st | - | 21st |
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| 6/27/2020 | Jackson Motorplex - Jackson, MN $30,000-to-win AGCO Jackson Nationals featuring the World of Outlaws 410 Sprints - Winged: World of Outlaws Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Jason Sides (410 Sprints - Winged) | 2nd | - | - | 18th |
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| 7/2/2020 | Cedar Lake Speedway - New Richmond, WI FVP Platinum Battery Showdown 410 Sprints - Winged: World of Outlaws 360 Sprints - Non-Winged: Traditional Sprint Car Series Dirt Super Late Models | Results | | Jason Sides (410 Sprints - Winged) | - | - | - | - |
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| 7/3/2020 | Cedar Lake Speedway - New Richmond, WI FVP Platinum Battery Showdown 410 Sprints - Winged: World of Outlaws Dirt Super Late Models | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | - | 15th |
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| 7/4/2020 | Cedar Lake Speedway - New Richmond, WI 410 Sprints - Winged: World of Outlaws Dirt Super Late Models | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 3rd | 17th |
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| 7/10/2020 | 34 Raceway - West Burlington, IA World of Outlaws NOS Energy Drink Sprint Cars 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | - | 12th |
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| 7/11/2020 | Wilmot Raceway - Wilmot, WI Badger 40 410 Sprints - Winged: World of Outlaws Lightning Sprints: IRA Lightning Sprints Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Jason Sides (410 Sprints - Winged) | 2nd | 5th | - | 10th |
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| 7/12/2020 | Terre Haute Action Track - Terre Haute, IN World of Outlaws NOS Energy Drink Sprint Cars 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | - | 18th |
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| 7/14/2020 | Attica Raceway Park - Attica, OH Ohio Logistics Brad Doty Classic 410 Sprints - Winged: World of Outlaws 410 Sprints - Non-Winged | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 3rd | 19th |
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| 7/21/2020 | Lernerville Speedway - Sarver, PA Don Martin Memorial Silver Cup 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 1st | 7th |
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| 7/23/2020 | Lincoln Speedway - Abbottstown, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 15th |
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| 7/24/2020 | Williams Grove Speedway - Mechanicsburg, PA Champion Racing Oil Summer Nationals 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 9th | - | 15th | - |
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| 7/25/2020 | Williams Grove Speedway - Mechanicsburg, PA Champion Racing Oil Summer Nationals 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 11th | - |
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| 8/7/2020 | Federated Auto Parts I-55 Raceway - Pevely, MO Night Before the Ironman 410 Sprints - Winged: World of Outlaws Midgets: POWRi DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 18th |
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| 8/8/2020 | Federated Auto Parts I-55 Raceway - Pevely, MO Ironman 55 410 Sprints - Winged: World of Outlaws Midgets: POWRi DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 1st | 16th |
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| 8/13/2020 | Knoxville Raceway - Knoxville, IA NOS Energy Drink Knoxville Nationals Presented by Casey's General Stores 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 1st | - | - | 14th |
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| 8/14/2020 | Knoxville Raceway - Knoxville, IA NOS Energy Drink Knoxville Nationals Presented by Casey's General Stores 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 2nd | - | 18th | - |
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| 8/15/2020 | Knoxville Raceway - Knoxville, IA NOS Energy Drink Knoxville Nationals Presented by Casey's General Stores 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | 8th | - |
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| 8/21/2020 | River Cities Speedway - Grand Forks, ND Second Leg of the World of Outlaws Northern Tour 410 Sprints - Winged: World of Outlaws B Modifieds, WISSOTA Late Model | Results | | Jason Sides (410 Sprints - Winged) | 2nd | 5th | - | 13th |
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| 8/22/2020 | Red River Valley Speedway - West Fargo, ND Red River Rumble 410 Sprints - Winged: World of Outlaws IMCA Stock Car | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 14th |
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| 8/29/2020 | US 36 Raceway - Osborn, MO 410 Sprints - Winged: World of Outlaws B Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | - | 12th |
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| 8/30/2020 | I-80 Speedway - Greenwood, NE 410 Sprints - Winged: World of Outlaws B Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 11th |
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| 9/5/2020 | Huset's Speedway - Brandon, SD NOS Energy Drink World of Outlaws Sprint Car Series 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 1st | 13th |
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| 9/6/2020 | Huset's Speedway - Brandon, SD NOS Energy Drink World of Outlaws Sprint Car Series 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 2nd | 22nd (DNF) |
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| 9/11/2020 | Dodge City Raceway Park - Dodge City, KS 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | - | 14th |
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| 9/12/2020 | Dodge City Raceway Park - Dodge City, KS 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 13th |
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| 9/18/2020 | Lawton Speedway - Lawton, OK 410 Sprints - Winged: World of Outlaws USRA Limited Mods | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 13th |
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| 9/19/2020 | Devil's Bowl Speedway - Mesquite, TX 410 Sprints - Winged: World of Outlaws USRA Limited Mods | Results | | Jason Sides (410 Sprints - Winged) | 2nd | 4th | - | 9th |
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| 9/24/2020 | Plymouth Speedway - Plymouth, IN 410 Sprints - Winged: World of Outlaws Street Stocks | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 15th |
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| 9/25/2020 | Wayne County Speedway - Orrville, OH 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 14th |
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| 9/26/2020 | Lernerville Speedway - Sarver, PA Commonwealth Clash 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 17th |
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| 10/2/2020 | Williams Grove Speedway - Mechanicsburg, PA Champion Racing Oil National Open 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 14th | 27th |
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| 10/3/2020 | Williams Grove Speedway - Mechanicsburg, PA Champion Racing Oil National Open 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 15th | - |
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| 10/9/2020 | Port Royal Speedway - Port Royal, PA Nittany Showdown 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 10th | - | - | - |
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| 10/10/2020 | Port Royal Speedway - Port Royal, PA Nittany Showdown 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 12th | - |
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| 10/16/2020 | Lakeside Speedway - Kansas City, KS FVP Platinum Battery Showdown 410 Sprints - Winged: World of Outlaws Mod Lites | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 1st | 17th |
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| 10/17/2020 | Lake Ozark Speedway - Eldon, MO 410 Sprints - Winged: World of Outlaws Street Stocks | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 19th |
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| 10/24/2020 | Kokomo Speedway - Kokomo, IN World of Outlaw Sprint Cars 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 3rd | 12th |
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| 11/6/2020 | The Dirt Track at Charlotte - Concord, NC Can-Am World Finals 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) | 10th | - | 24th | 27th |
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| 11/7/2020 | The Dirt Track at Charlotte - Concord, NC Can-Am World Finals 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) | 5th | - | - | 23rd |
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